Benzoic acid, 2-(isocyanatosulfonyl)-, ethyl ester → Ethyl 2-(4-methylamino-6-trifluoromethoxy-1,3,5-triazin-2-ylaminocarbonylaminosulfonyl)benzoate

HRID 1198291Notes

Reaction equation

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

Participants

Conditions

Temperature: 22 °C

Procedure

3.1 g (0.012 mol) of 2-carboethoxybenzenesulfonyl isocyanate in 3 ml of methylene chloride were added over the course of 10 minutes to a stirred mixture of 2.5 g (0.012 mol) of 2-amino-4-methylamino-6-trifluoromethoxy-1,3,5-triazine and 150 ml of methylene chloride at 22° C., and the mixture was stirred at 22° C. for 30 hours. It was then concentrated under reduced pressure, stirred with methyl tert-butyl ether and filtered off with suction. Further washing with methanol and drying resulted in 3.8 g (67.4% of theory) of the title compound of melting point 182°-184° C. (decomposition).

Workup

concentrationIt was then concentrated under reduced pressure
stirringstirred with methyl tert-butyl ether
filtrationfiltered off with suction
washFurther washing with methanol
customdrying

Sources & evidence

ORD record: ord-663b67f30a36434796958ab105ef76b2
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05280118

Reaction notes

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