Dimethyl Sulfoxide → HCID 11277604, compound

HRID 1370771Notes

Reaction equation

HRID 1370771 reaction equation
[CH3:1][O:2][N:3]([CH3:20])[C:4](=[O:19])[CH:5]=[CH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[CH3:21]S(C)=O>[H-].[Na+]>[CH3:1][O:2][N:3]([CH3:20])[C:4]([C@@H:5]1[CH2:21][C@H:6]1[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[CH:9][CH:8]=1)=[O:19]

Participants

4

Reactant 2

HCID 679Dimethyl Sulfoxide2×HCID 73195160HCID 73195160, compound

Product 1

HCID 11277604HCID 11277604, compound

Reagents, catalysts & solvents 1

HCID 24758Sodium hydrideSolvent

Conditions

Temperature
50 °C

Procedure

5.8 g (21.4 mmol) of the compound obtained in Step F dissolved in 30 ml of DMSO are added to a suspension of ylid produced starting from 10.6 g (2 eq) of Me3SOI dissolved while hot in 50 ml of DMSO and 1.25 g of NaH. After 15 hours' stirring at room temperature and 4 hours at 50° C., the title cyclopropane amide is obtained in the form of a brown oil.

Workup

  1. additionare added to a suspension of ylid
  2. customproduced

Sources & evidence

ORD record
ord-7165d8864abb4a098e060a135a9e4e7c
Source dataset
uspto-grants-2003_06
Patent number
US06583319B1

Reaction notes

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