2-Amino-4,6-dimethoxypyrimidine → Amidosulfuron

HRID 466746

Reaction equation

HRID 466746 reaction equation
[CH3:1][S:2]([N:5]([S:7]([NH:10][C:11](=[O:15])OCC)(=[O:9])=[O:8])[CH3:6])(=[O:4])=[O:3].[NH2:16][C:17]1[N:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[N:18]=1>ClC1C=CC=CC=1>[CH3:1][S:2]([N:5]([S:7]([NH:10][C:11]([NH:16][C:17]1[N:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[N:22]=1)=[O:15])(=[O:8])=[O:9])[CH3:6])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 53920146ethyl (N-methylsulfonyl-N-methylamino)sulfonylcarbamate

Product 1

HCID 91777AmidosulfuronYield 98.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

52.0 g of ethyl (N-methylsulfonyl-N-methylamino)sulfonylcarbamate are dissolved in 500 ml of chlorobenzene, 31.0 g of 2-amino-4,6-dimethoxypyrimidine are added at room temperature with stirring, and the mixture is heated at 80° C. for 3 hours. After cooling to 0° C., the precipitate is filtered off and washed with 100 ml of chlorobenzene. 72.7 g of the desired product of a purity of 98.5% are obtained, which corresponds to a yield of 97.2% of theory. The melting point of the product is 185°-186° C.

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationthe precipitate is filtered off
  3. washwashed with 100 ml of chlorobenzene

Sources & evidence

ORD record
ord-d48bee073d7c40ca8d0f0d2d309a7740
Source dataset
uspto-grants-1992_10
Patent number
US05157121

Linked notes

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