Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → 2-[[(2,6-Dimethoxy-5-nitropyrimidin-4-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester

HRID 4132

Reaction equation

HRID 4132 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([O:13][CH3:14])[N:4]=1.[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([N:28]=[C:29]=[O:30])(=[O:27])=[O:26])([O:17][CH3:18])=[O:16]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][C:29]([NH:28][S:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:15]([O:17][CH3:18])=[O:16])(=[O:27])=[O:26])=[O:30])[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([O:13][CH3:14])[N:4]=1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 2399532,6-Dimethoxy-5-nitropyrimidin-4-amine

Product 1

HCID 140502032-[[(2,6-Dimethoxy-5-nitropyrimidin-4-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl esterYield 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.2 g (1.0 mmol) of 2,6-dimethoxy-5-nitro-4-pyrimidinamine and 0.6 g (2.4 mmol) of 2-carbomethoxybenzenesulfonyl isocyanate in 15 ml of methylene chloride was stirred at ambient temperature and pressure for 12 hours under anhydrous conditions. The solvent was then evaporated under reduced pressure. The residue was stirred in n-butyl chloride (70 ml). The solid was then collected by filtration, washed with ether and then dried in an oven to afford 0.4 g of the title compound, m.p. 150°-152° dec.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. filtrationThe solid was then collected by filtration
  3. washwashed with ether
  4. customdried in an oven

Sources & evidence

ORD record
ord-9ecd5cb885984a4aae7b8025b84f1e4f
Source dataset
uspto-grants-1988_02
Patent number
US04723991

Linked notes

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