Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → Methyl 2-(4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-ylaminocarbonylaminosulfonyl)benzoate

HRID 249413Notes

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]([O:24][CH3:25])[N:21]=[C:20]([O:26][C:27]([F:30])([F:29])[F:28])[N:19]=1>ClCCCl>[CH3:25][O:24][C:22]1[N:21]=[C:20]([O:26][C:27]([F:30])([F:28])[F:29])[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

Conditions

Temperature: 22 °C

Procedure

3.6 g (0.015 mol) of 2-carbomethoxybenzenesulfonyl isocyanate in 4 ml of 1,2-dichloroethane were added over the course of 5 minutes to a stirred mixture of 3.15 g (0.015 mol) of 2-amino-4-methoxy-6-trifluoromethoxy-1,3,5-triazine and 150 ml of 1,2-dichloroethane at 22° C., and the mixture was stirred at 22° C. for 12 hours. It was then concentrated under reduced pressure and crystallized using 1:1 methyl tert-butyl ether/petroleum ether, and the product was filtered off with suction and washed with petroleum ether to yield 5.1 g (75.4% of theory) of the title compound of melting point 149° C. (decomposition).

Workup

concentrationIt was then concentrated under reduced pressure
customcrystallized
filtrationthe product was filtered off with suction
washwashed with petroleum ether

Sources & evidence

ORD record: ord-2f9d5849b1294e929f2a8d44a99c9403
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05214143

Reaction notes

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