Dimethyl Sulfide → HCID 15539134, compound

HRID 382773Notes

Reaction equation

HRID 382773 reaction equation
O=[O+][O-].C=[C:5]1[CH2:10][N:9]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:8][N:7]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:6]1.C(=O)=[O:36].CC(C)=O.CSC>O=O.CC(C)=O>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:9]2[CH2:10][C:5](=[O:36])[CH2:6][N:7]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:8]2)(=[O:13])=[O:12])=[CH:15][CH:16]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 15539133HCID 15539133, compoundHCID 18522661Acetone cardice

Product 1

HCID 15539134HCID 15539134, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 977OxygenSolvent

Procedure

A stream of ozone in oxygen was bubbled into a solution of hexahydro-5-(methylene)-1,3-bis(4-nitrobenzenesulfonyl)pyrimidine (0.6 g, 1.3 mmol) in 150 mL acetone at −78° C. (dry ice-acetone bath) until a blue color persisted for 5 minutes. The reaction was stirred for 15 minutes under a nitrogen atmosphere. Next, 2.0 mL of dimethyl sulfide was added. After stirring for 10 minutes, the solvent was removed and the solid dried under reduced pressure to give 0.5 g (83%) of tetrahydro-1,3-bis(4-nitrobenzenesulfonyl)pyrimidin-5(4H)-one. [1H NMR (acetone-d6): δ 3.95 (s, 4 H), 5.25 (s, 2 H), 8.20, 8.48 (AB q, J=9.0 Hz, 8 H); 13C NMR (DMSO-d6): δ 53.8, 58.8, 124.8, 129.3, 141.9, 150.4, 196.2].

Workup

  1. stirringAfter stirring for 10 minutes
  2. customthe solvent was removed
  3. customthe solid dried under reduced pressure

Sources & evidence

ORD record
ord-822a63c423954e95b8dbbdb4dfb3535b
Source dataset
uspto-grants-2001_10
Patent number
US06310204B1

Reaction notes

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