Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → N-(2-Methoxycarbonylphenyl-sulfonyl)-N'-(4-methoxy-6-ethoxythiocarbonylthiomethyl-pyrimidin-2-yl)-urea

HRID 980761Notes

Reaction equation

HRID 980761 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH2:10][S:11][C:12]([O:14][CH2:15][CH3:16])=[S:13])[N:3]=1.[CH3:17][O:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([N:30]=[C:31]=[O:32])(=[O:29])=[O:28])=[O:20]>C(#N)C>[CH3:17][O:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([NH:30][C:31]([NH:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH2:10][S:11][C:12]([O:14][CH2:15][CH3:16])=[S:13])[N:3]=1)=[O:32])(=[O:28])=[O:29])=[O:20]

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 542237212-Amino-4-methoxy-6-ethoxythiocarbonylthiomethyl-pyrimidine

Product 1

HCID 20070851N-(2-Methoxycarbonylphenyl-sulfonyl)-N'-(4-methoxy-6-ethoxythiocarbonylthiomethyl-pyrimidin-2-yl)-urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.0 g of 2-amino-4-methoxy-6-ethoxythiocarbonylthiomethyl-pyrimidine and 6.5 g of 2-methoxycarbonylphenylsulfonylisocyanate are suspended in 20 ml of abs. acetonitrile, and the suspension is stirred at 20° to 26° C. for 2 hours. A clear solution is firstly formed during this time, and the final product subsequently crystallises out. To isolate the final product, the reaction mixture is cooled to 0° C. and then filtered. The yield is 9.0 g (67% of theory) of N-(2-methoxycarbonylphenyl-sulfonyl)-N'-(4-methoxy-6-ethoxythiocarbonylthiomethyl-pyrimidin-2-yl)-urea, m.p. 160°-162° C. (decomp.).

Workup

  1. customA clear solution is firstly formed during this time
  2. customthe final product subsequently crystallises out

Sources & evidence

ORD record
ord-12b01ea16d6c4fb6b2577a896a599292
Source dataset
uspto-grants-1987_01
Patent number
US04639264

Reaction notes

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