Dimethylformamide → HCID 69127893, compound

HRID 661735Notes

Reaction equation

HRID 661735 reaction equation
[H-].[Na+].CN(C=O)C.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[SH:15].[C:16]1([N:22]=[C:23]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:24]=[CH:25]S(C2C=CC=CC=2)(=O)=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C.O>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15][CH:25]=[CH:24][C:23](=[N:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 805982-BromobenzenethiolHCID 86617322HCID 86617322, compound

Product 1

HCID 69127893HCID 69127893, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil: 0.026 g) was suspended to DMF (2 ml), and 2-bromothiophenol (0.10 g) was added thereto under ice-cooling. Furthermore, phenyl N-phenyl-3-(phenylsulfonyl)acrylimidate (0.20 g) was added thereto, and stirred for one hour under ice-cooling. After the reaction, water and ethyl acetate were added to the reaction mixture, and extracted. The organic layer was washed with aqueous saturated sodium chloride solution, dried, and distilled off the solvent. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain phenyl 3-(2-bromophenylthio)-N-phenylacrylimidate (0.19 g).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. temperaturecooling
  4. additionwere added to the reaction mixture
  5. extractionextracted
  6. washThe organic layer was washed with aqueous saturated sodium chloride solution
  7. customdried
  8. distillationdistilled off the solvent

Sources & evidence

ORD record
ord-56abf2cb394049fc91317197296c7941
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

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