Chlorosulfonic acid → HCID 86595526, compound

HRID 901936Notes

Reaction equation

HRID 901936 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)=[N:5][C:4]=1[S:25][CH3:26])#[N:2].[Cl:27][S:28](O)(=[O:30])=[O:29]>C(Cl)(Cl)Cl>[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:11]=[CH:12][C:13]([S:28]([Cl:27])(=[O:30])=[O:29])=[CH:14][CH:15]=2)[C:6]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH3:24])=[CH:20][CH:21]=2)=[N:5][C:4]=1[S:25][CH3:26])#[N:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 69220498HCID 69220498, compound

Product 1

HCID 86595526HCID 86595526, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-cyano-2-(4-ethoxyphenyl)-1-phenyl-4-(methylthio)-6-oxo-1,6-dihydropyrimidine (1 g, 2.7 mmol) in chlorosulfonic acid (6.14 g, 53 mmol) and chloroform (30 ml) was refluxed 1 hr and then poured on to ice. The chloroform layer was collected and dried over Na2SO4 and concentrated under vacuo to yield title compound (0.8 g, yield 62.9%). 1H-NMR (DMSO):δ 1.21-1.24 (t, 3H), 2.6 (s, 3H), 3.94-3.99 (q, 2H), 6.7-6.72 (d, 1H), 7.03-7.05 (q, 1H), 7.33-7.39 (m, 5H), 8.04-8.05 (1H). MS m/z:463.7 (M+).

Workup

  1. additionpoured on to ice
  2. customThe chloroform layer was collected
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-db4cad3b13e14996b27d291537cb7ff7
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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