Potassium Carbonate → N-(2-Methoxycarbonylbenzyl)sulfonyl-N'-(4,6-dimethoxy-2-pyrimidinyl) thiourea

HRID 330452Notes

Reaction equation

HRID 330452 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[CH2:7][S:8]([NH2:11])(=[O:10])=[O:9])=[O:4].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([N:26]=[C:27]=[S:28])[N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[CH2:7][S:8]([NH:11][C:27]([NH:26][C:20]1[N:19]=[C:18]([O:17][CH3:16])[CH:23]=[C:22]([O:24][CH3:25])[N:21]=1)=[S:28])(=[O:10])=[O:9])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13958774Benzoic acid, 2-[(aminosulfonyl)methyl]-, methyl esterHCID 142539422-Isothiocyanato-4,6-dimethoxypyrimidine

Product 1

HCID 14275714N-(2-Methoxycarbonylbenzyl)sulfonyl-N'-(4,6-dimethoxy-2-pyrimidinyl) thioureaYield 771.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2.5 g of (2-methoxycarbonylbenzyl)sulfonamide, 21.5 g of 4,6-dimethoxy-2-isothiocyanatopyrimidine and 15.1 g of anhydrous potassium carbonate in 400 ml of acetone is stirred for 8.5 hours at 55° C., and then filtered to collect precipitated crystals. To the filtrate, further 2 g of anhydrous potassium carbonate is added and stirred for 2 hours at 60° C. The precipitated crystals are collected. The combined crystals are suspended in 1.5 of water and adjusted to pH 2 with hydrochloric acid. After stirring the mixture for an hour, the crystals are collected by filtration, washed with water, dried and recrystallized from acetonitrile to give 35.9 g of the title compound, as white powder.

Workup

  1. filtrationfiltered
  2. customto collect
  3. customprecipitated crystals
  4. additionTo the filtrate, further 2 g of anhydrous potassium carbonate is added
  5. stirringstirred for 2 hours at 60° C
  6. customThe precipitated crystals are collected
  7. stirringAfter stirring the mixture for an hour
  8. filtrationthe crystals are collected by filtration
  9. washwashed with water
  10. customdried
  11. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-adf9623f21264d849317f0cc946ae599
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Reaction notes

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