Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → N-(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)urea

HRID 462347Notes

Reaction equation

HRID 462347 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12])=[O:4].[NH2:17][C:18]1[N:23]=[C:22]([CH:24]2[CH2:26][CH2:25]2)[N:21]=[C:20]([O:27][CH3:28])[N:19]=1>C(Cl)Cl>[CH:24]1([C:22]2[N:21]=[C:20]([O:27][CH3:28])[N:19]=[C:18]([NH:17][C:15]([NH:14][S:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:3]([O:2][CH3:1])=[O:4])(=[O:12])=[O:13])=[O:16])[N:23]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 27265914-Cyclopropyl-6-methoxy-1,3,5-triazin-2-amine

Product 1

HCID 19758555N-(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 g of 2-methoxycarbonylbenzenesulfonylisocyanate are added with stirring, under a nitrogen atmosphere, to a solution of 1.3 g of 2-amino-4-cyclopropyl-6-methoxy-1,3,5-triazine in 10 ml of CH2Cl2. A slight exothermic reaction occurs, which soon however subsides. Stirring is maintained for 14 hours at room temperature, and the solution is then caused to crystallise by the addition of ether. The precipitate is filtered off and dried. The yield is 2.3 g of the above urea, which melts at 166°-168° C.

Workup

  1. customA slight exothermic reaction
  2. customto crystallise by the addition of ether
  3. filtrationThe precipitate is filtered off
  4. customdried

Sources & evidence

ORD record
ord-699980c8c3074e1fa6ddcd448b023cbb
Source dataset
uspto-grants-1985_05
Patent number
US04515626

Reaction notes

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