Methanol → 2-(3-Cyclohexyl-2,4,6-trioxotetrahydropyrimidin-1(2H)-yl)benzene-1-sulfonyl fluoride

HRID 441701Notes

Reaction equation

HRID 441701 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][C:3](Cl)=[O:4].[CH:8]1([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([F:27])(=[O:26])=[O:25])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CO>C(Cl)(Cl)Cl>[CH:8]1([N:14]2[C:3](=[O:4])[CH2:2][C:1](=[O:6])[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:24]([F:27])(=[O:26])=[O:25])[C:15]2=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 74269Propanedioyl dichlorideHCID 214172322-[(Cyclohexylcarbamoyl)amino]benzene-1-sulfonyl fluoride

Product 1

HCID 214172312-(3-Cyclohexyl-2,4,6-trioxotetrahydropyrimidin-1(2H)-yl)benzene-1-sulfonyl fluorideYield 76.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Malonyldichloride (168 g, 1.2 mole) was added with stirring to N-cyclohexyl-N'-(2-fluorosulphonylphenyl)urea (270 g, 0.9 mole) in dry chloroform (1500 ml). This mixture was heated for 6 hours at 40°-50° C. and then cooled below 20° C., whereupon 300 ml of methanol were added cautiously. The reaction mixture was then evaporated under reduced pressure yielding 253 g of 1-cyclohexyl-3-(2-fluorosulphonylphenyl)barbituric acid. This sulphofluoride was converted into the sulphonamide as described under b) with a nearly quantitative yield.

Workup

  1. temperatureThis mixture was heated for 6 hours at 40°-50° C.
  2. additionwere added cautiously
  3. customThe reaction mixture was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-bb9014de022e4100b01d81a5820a83a6
Source dataset
uspto-grants-1977_08
Patent number
US04042397

Reaction notes

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