2-Amino-4,6-dimethyl pyrimidine → Sulfometuron-methyl

HRID 463973

Reaction equation

HRID 463973 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][O:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21])=[O:13]>C(#N)C>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:24]([NH:23][S:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:12]([O:11][CH3:10])=[O:13])(=[O:22])=[O:21])=[O:25])[N:3]=1

Participants

4

Reactant 2

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 52997Sulfometuron-methyl

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 37 g. of 2-amino-4,6-dimethylpyrimidine in 500 ml of anhydrous acetonitrile was added 67 g of 2-methoxycarbonylbenzenesulfonylisocyanate with stirring at ambient temperatures. The resulting mixture was thereafter stirred for sixteen hours and then filtered to remove the desired product which had precipitated as a white solid, m.p. 198°-202°. It showed infrared absorption peaks at 1750, 1700, 1600 and 1500 cm-1, consistent for the desired compound.

Workup

  1. stirringThe resulting mixture was thereafter stirred for sixteen hours
  2. filtrationfiltered
  3. customto remove the desired product which
  4. customhad precipitated as a white solid, m.p. 198°-202°
  5. customabsorption peaks at 1750, 1700, 1600 and 1500 cm-1

Sources & evidence

ORD record
ord-55f2a782799e41e2bd8a231de203d7b0
Source dataset
uspto-grants-1985_10
Patent number
US04545808

Linked notes

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