Reaction #2419

Reaction equation

acetone

oleum

4,4'-diamino-6-carbamoyl benzanilide

NH4OH

→

4,4'-diamino-6-cyanobenzanilide

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturealready cooled down to -5° to 0° C
2. 2
   WashThe solution was sufficiently washed
3. 3
   Otherto remove salt
4. 4
   Filtrationby filtering
5. 5
   Washwashed with a small amount of warm ethanol
6. 6
   Otherdried in a vacuum oven at 80° C
7. 7
   workup.ADDITIONThe dried reactant which was mixed with by-products
8. 8
   Extractionwas extracted by soxlet
9. 9
   workup.ADDITIONtreated with the activated carbon
10. 10
    workup.ADDITIONethanol was added
11. 11
    Otherto recrystallize in the mixture solvent (acetone:ethanol=1:1)
12. 12
    FiltrationThe light yellow-scalelike crystal was filtered
13. 13
    Otherdried in a vacuum oven at 80° C
14. 14
    ExtractionThe light yellow-scalelike crystal was extracted again by soxlet with acetone
15. 15
    workup.ADDITIONtreated with the activated carbon
16. 16
    OtherAnd then the white-scalelike crystal obtained
17. 17
    Dryingwas dried in a vacuum oven at 80° C. (40 g of the raw material
18. 18
    Otherwas obtained
19. 19
    Otherthereof was 250° to 251° C.

Procedure

350 ml of oleum (30% by weight) was cooled down below 0° C. using an ice bath, 99.6 g (0.368 mol) of 4,4'-diamino-6-carbamoyl benzanilide in a powder form was added below 5° C. with stirring. The stirring was continued to the next day, and the solution was neutralized by adding 1100 ml of NH4OH (28% by weight) already cooled down to -5° to 0° C. The solution was sufficiently washed to remove salt by filtering and washed with a small amount of warm ethanol and then dried in a vacuum oven at 80° C. The dried reactant which was mixed with by-products was extracted by soxlet and treated with the activated carbon and then ethanol was added to recrystallize in the mixture solvent (acetone:ethanol=1:1). The light yellow-scalelike crystal was filtered and dried in a vacuum oven at 80° C. The light yellow-scalelike crystal was extracted again by soxlet with acetone and treated with the activated carbon. And then the white-scalelike crystal obtained by recrystalling in the mixture solvent (acetone:ethanol=1:1) was dried in a vacuum oven at 80° C. (40 g of the raw material was obtained and the boiling point thereof was 250° to 251° C.).

Source