Dimethyl Sulfoxide → 1-bromo-N-[(1-formyl)propyl]-cyclopropane-1-carboxamide

HRID 1349371Notes

Reaction equation

HRID 1349371 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].CS(C)=O.[Br:11][C:12]1([C:15]([NH:17][CH2:18][CH2:19][CH2:20]CO)=[O:16])[CH2:14][CH2:13]1.[Cl-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[Br:11][C:12]1([C:15]([NH:17][CH:18]([CH:2]=[O:3])[CH2:19][CH3:20])=[O:16])[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 65578Oxalyl chlorideHCID 694261281-bromo-N-[(1-hydroxymethyl)propyl]-cyclopropane-1-carboxamide

Product 1

HCID 180008601-bromo-N-[(1-formyl)propyl]-cyclopropane-1-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

2.23 ml of oxalyl chloride in 102 ml of methylene chloride is mixed drop by drop at −78° C. under nitrogen with 3.6 ml of dimethylsulfoxide in 41 ml of methylene chloride. Then, 5.43 g of amide alcohol 78 in 41 ml of methylene chloride and, after 15 minutes, 14.3 ml of triethylamine are added in drops at −78° C. After another 30 minutes, sodium chloride solution is added, extracted with methylene chloride, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 3.4 g of 1-bromo-N-[(1-formyl)propyl]-cyclopropane-1-carboxamide 79 is obtained as a yellow oil, which is converted into title compound 80 analogously to the reaction of amide 76.

Workup

  1. extractionextracted with methylene chloride
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-5453a7bfd7d3470f8624493d5cddea08
Source dataset
uspto-grants-2007_05
Patent number
US07211680B2

Reaction notes

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