Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → Methyl 2-[(4-methoxy-6-methyl-pyrimidin-2-yl)carbamoylsulfamoyl]benzoate
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[CH3:11][O:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22])=[O:14]>C(Cl)Cl>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:25]([NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:13]([O:12][CH3:11])=[O:14])(=[O:23])=[O:22])=[O:26])[N:7]=1Participants
Procedure
To a stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 30 ml of anhydrous methylene chloride was added at ambient temperature 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate. After stirring for 16 hours, the foregoing mixture was filtered to remove unreacted amine, and the filtrate evaporated at temperatures up to 40° and reduced pressure. The resultant residue was stirred in 25 ml of water, the pH adjusted to 10 by the addition of 50% sodium hydroxide and the solution filtered. Acidification of the filtrate to pH 3 with hydrochloric acid caused precipitation of the desired product which was removed by filtration and dried to yield 0.8 g of product melting at 173°-179°. It showed infrared absorption peaks at 1720, 1680, 1630 and 1550 cm-1, consistent for N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide.
Workup
- filtrationthe foregoing mixture was filtered
- customto remove unreacted amine
- customthe filtrate evaporated at temperatures up to 40°
- stirringThe resultant residue was stirred in 25 ml of water
- additionthe pH adjusted to 10 by the addition of 50% sodium hydroxide
- filtrationthe solution filtered
- customprecipitation of the desired product which
- customwas removed by filtration
- customdried
Sources & evidence
- ORD record
- ord-edc0f5acaf4947b28f35fed128535740
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04591378
Reaction notes
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