Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → 2-[[[4-(Methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester

HRID 329557Notes

Reaction equation

HRID 329557 reaction equation
[C:1]([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:3][CH3:4])=[O:2].[NH2:17][C:18]1[N:23]=[C:22]([NH:24][CH3:25])[N:21]=[C:20]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])[N:19]=1>C(Cl)Cl>[CH3:25][NH:24][C:22]1[N:21]=[C:20]([O:26][CH2:27][C:28]([F:31])([F:29])[F:30])[N:19]=[C:18]([NH:17][C:15]([NH:14][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:1]([O:3][CH3:4])=[O:2])(=[O:12])=[O:13])=[O:16])[N:23]=1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 1375559STK076603

Product 1

HCID 156111062-[[[4-(Methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Carbomethoxybenzenesulfonyl isocyanate (0.5 g) was dissolved in 5 ml of methylene chloride. The aminoheterocycle (0.46 g) prepared in Example 2 was added and the mixture was stirred overnight under nitrogen at room temperature. The resulting solids were filtered of, washed with methylene chloride and dried to give 0.54 g of ~80% pure subject compound; m.p. 195°-197° C. decomp. No attempt was made at further purification. The resulting product named above had the following characteristics: IR (nujol) showed carbonyl bands at 1723 cm-1 and 1740 cm-1. NMR (CDCl3, DMSO-d6): δ2.9, m, (NHCH3); 3.8, s, (CO2CH3); 4.9, m, (OCH2CF3); 7.7-8.4 m, (aromatic H's) plus ~20% heterocycle.

Workup

  1. filtrationThe resulting solids were filtered of,
  2. washwashed with methylene chloride
  3. customdried

Sources & evidence

ORD record
ord-0edd3f64f64346218ee6864605222d1e
Source dataset
uspto-grants-1990_01
Patent number
US04892575

Reaction notes

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