Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → Methyl 2-(4-fluoro-6-trifluoromethoxy-2-pyrimidinylaminocarbonylaminosulfonyl)benzoate

HRID 1978157Notes

Reaction equation

HRID 1978157 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]([F:24])[CH:21]=[C:20]([O:25][C:26]([F:29])([F:28])[F:27])[N:19]=1>ClCCCl>[F:24][C:22]1[CH:21]=[C:20]([O:25][C:26]([F:29])([F:27])[F:28])[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:3]([O:2][CH3:1])=[O:4])(=[O:12])=[O:13])=[O:16])[N:23]=1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 150227162-Amino-4-fluoro-6-trifluoromethoxypyrimidine

Product 1

HCID 15022724Methyl 2-(4-fluoro-6-trifluoromethoxy-2-pyrimidinylaminocarbonylaminosulfonyl)benzoate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

3.6 g (0.015 mol) of 2-methoxycarbonylbenzenesulfonyl isocyanate in 15 ml of 1,2-dichloroethane were added over the course of 15 minutes to a stirred mixture of 2.95 g (0.015 mol) of 2-amino-4-fluoro-6-trifluoromethoxypyrimidine and 100 ml of 1,2-dichloroethane at 25° C., and the mixture was stirred at 25° C. for 12 hours. The solution was concentrated under reduced pressure, and the residue was stirred with 1:1 ether/petroleum ether. Filtration with suction and drying yielded 4.8 g (73.3% of theory) of the title compound of melting point 157-161° C.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. stirringthe residue was stirred with 1:1 ether/petroleum ether
  3. filtrationFiltration with suction
  4. customdrying

Sources & evidence

ORD record
ord-18dbc4c6c1f34bbe8b0e894e4f7c745f
Source dataset
uspto-grants-2001_05
Patent number
US06235904B1

Reaction notes

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