Reaction #4231

Reaction equation

2-amino-4-methoxy-6-methyl-1,3,5-triazine

2-(Dichloromethyl)benzenesulfonyl isocyanate

→

white solid

2-(Dichloromethyl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otheras described in the synthesis of Example 1
2. 2
   Filtrationand filtered
3. 3
   OtherThe filtrate was evaporated
4. 4
   Otherrecrystallized from acetone

Procedure

2-(Dichloromethyl)benzenesulfonyl isocyanate prepared from 10 mmol of sulfonamide as described in the synthesis of Example 1, was treated with acetonitrile (15 ml) and 2-amino-4-methoxy-6-methyl-1,3,5-triazine (1.40 g). The mixture was stirred for 18 hrs. and filtered. The filtrate was evaporated and recrystallized from acetone to give 0.78 g of white solid, mp 168°-169° (dec). 1H nmr δDMSO-d6TMS 8.37-7.50 (m, featuring singlet at 8.07), 7.00-6.17 (brds), 4.00 (s), 2.48 (s). IR (nujol) featured bands at 1720 and 1590 cm-1. Mass spectrum featured 264.9367 (calc'd for C8H5Cl2NO3S 264.9367) and 140.0687 (calc'd for C5H8N4O 140.0697).

Source