Reaction #450877

Reaction equation

3-hydroxybenzylamine

N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea

→

title compound

N,N'-Bis(t-butoxycarbonyl)-N"-(3-hydroxyphenyl)methylguanidine

Solvents

water

DMF

Conditions

Workup

1. 1
   Filtrationthe solids collected by filtration
2. 2
   Filtrationfiltered
3. 3
   Otherto remove silver salts
4. 4
   Otherchromatographed on silica gel with 10% ethyl acetate in dichloromethane
5. 5
   OtherRecrystallization

Procedure

3-hydroxybenzylamine, prepared as above (1.23 g) and N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea (2.90 g) were combined in 100 mL DMF, and silver acetate (2.9 g) was added in three portions over 30 min with mechanical stirring. The mixture became thick and a yellow color developed. After 1 hr, the mixture was diluted with 300 mL water, and the solids collected by filtration, re-suspended in dichloromethane, filtered to remove silver salts, and chromatographed on silica gel with 10% ethyl acetate in dichloromethane. Recrystallization provided the title compound as a white solid, mp 169°-172° C. (dec) (2.2 g, 61%).

Source