Thionyl Chloride → N-[1-(4-Bromo-phenyl)-cyclopropanecarbonyl]-methanesulfonamide

HRID 45599Notes

Reaction equation

HRID 45599 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:18][S:19]([NH2:22])(=[O:21])=[O:20].[H-].[Na+]>C(Cl)Cl.C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([NH:22][S:19]([CH3:18])(=[O:21])=[O:20])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 66577406N-[1-(4-Bromo-phenyl)-cyclopropanecarbonyl]-methanesulfonamideYield 86.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid (22 g, 91.3 mmol) and SOCl2 (13.6 mL, 183 mmol) in CH2Cl2 were heated together for 1.5 hours then evaporated to afford a dark oil. This oil was added via syringe over 30 minutes to a mixture of MeSO2NH2 (19 g, 200 mmol) in THF (250 mL) that was pre-treated at room temperature with NaH (60% in oil; 8.0 g, 200 mmol) for 1.5 hours. After a further 20 minutes, the mixture was poured into water, acidified and extracted with CH2Cl2, washed with water (2×) and evaporated to ˜100 mL. Hexane (300 mL) was added and the product collected by filtration to yield the title compound (25 g).

Workup

  1. customthen evaporated
  2. customto afford a dark oil
  3. extractionextracted with CH2Cl2
  4. washwashed with water (2×)
  5. customevaporated to ˜100 mL
  6. additionHexane (300 mL) was added
  7. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-c0d81d75474948ff90c80476fd5f2cab
Source dataset
uspto-grants-2013_09
Patent number
US08541587B2

Reaction notes

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