Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl ester → Amidosulfuron

HRID 466254

Reaction equation

HRID 466254 reaction equation
[CH3:1][S:2]([N:5]([S:7]([NH2:10])(=[O:9])=[O:8])[CH3:6])(=[O:4])=[O:3].[CH3:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[N:16]=[C:15]([NH:21][C:22](=O)[O:23]C2C=CC=CC=2)[N:14]=1>C(#N)C>[CH3:1][S:2]([N:5]([S:7]([NH:10][C:22]([NH:21][C:15]1[N:14]=[C:13]([O:12][CH3:11])[CH:18]=[C:17]([O:19][CH3:20])[N:16]=1)=[O:23])(=[O:9])=[O:8])[CH3:6])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 11084607Methanesulfonamide, N-(aminosulfonyl)-N-methyl-

Product 1

HCID 91777AmidosulfuronYield 98.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

37.6 g of (N-methylsulfonyl-N-methylamino)sulfonamide are dissolved in 500 ml of acetonitrile, 55.0 g of phenyl 4,6-dimethoxy-2-pyrimidylcarbamate are added dropwise at room temperature, and the mixture is stirred for 18 hours at room temperature. Approx. 400 ml of acetonitrile are distilled off, and then 200 ml of water are added at 0° C., and the mixture is brought to pH 2-3 using 2N HCl. The product which has precipitated is filtered off with suction and washed with water. 72.6 g of the desired product of a purity of 98.4% are obtained, which corresponds to a yield of 96.8% of theory. The melting point of the product is 185-186° C.

Workup

  1. distillationApprox. 400 ml of acetonitrile are distilled off
  2. addition200 ml of water are added at 0° C.
  3. customThe product which has precipitated
  4. filtrationis filtered off with suction
  5. washwashed with water

Sources & evidence

ORD record
ord-02e82f3055f041f892d599eb871cbcfc
Source dataset
uspto-grants-1992_10
Patent number
US05155222

Linked notes

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