Sodium Cyanide → HCID 17882361, compound

HRID 369412Notes

Reaction equation

HRID 369412 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[N:10]([CH3:23])[C:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1.[C:29]([Cu])#[N:30].[C-]#N.[Na+]>CN(C=O)C>[C:29]([C:2]1[CH:3]=[C:4]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[N:10]([CH3:23])[C:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)#[N:30]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 70100389HCID 70100389, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 17882361HCID 17882361, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{3-Bromo-4-[5-(4-methylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl]phenyl}methanesulfonamide (320 mg, 0.69 mmol) was dissolved in DMF. CuCN (120 mg, 1.38 mmol) was added and the suspension was refluxed for 4 h. The mixture was cooled to room temperature, and NaCN (2.0 g in 10 ml of water) was added. After 0.5 h the mixture was extracted with ethyl acetate and the extracts were washed with water, and brine, and dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by preparatory TLC (hexane-ethyl acetate) to give N-{3-cyano-4-[5-(4-methylbenzoyl)-1-methyl-1H-pyrrol-2-yl-methyl]phenyl}methanesulfonamide (190 mg, 67%) as a solid, mp 171-172° C.

Workup

  1. temperaturethe suspension was refluxed for 4 h
  2. extractionAfter 0.5 h the mixture was extracted with ethyl acetate
  3. washthe extracts were washed with water, and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by preparatory TLC (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4bc855f9de26436aad534ade64c42e95
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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