Tributylstannane → HCID 19887196, compound

HRID 654404Notes

Reaction equation

HRID 654404 reaction equation
[CH2:1]([N:5]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[C:6](=[O:15])[CH:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH:3][CH3:4].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[CH2:3]([CH:2]1[CH2:1][N:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:6](=[O:15])[CH:7]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 54049845HCID 54049845, compound

Product 1

HCID 19887196HCID 19887196, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(2-Butenyl)-N-(3-trifluoromethylphenyl)-2-chloro-2-phenylacetamide (1.5 g) was added to 15 ml of benzene, followed by the addition of 1.2 g of tributyltin hydride and an extremely small amount of α,α-azobisisobutyronitrile (AIBN) under stirring at the refluxing temperature. After the reaction mixture was continuously stirred for 70 minutes, 40 ml of saturated saline were added, followed by extraction with toluene. After the extract was dried over anhydrous magnesium sulfate, the extract was concentrated in an evaporator and then subjected to chromatography on a silica gel column. The 3,4-trans isomer (0.67 g) and the 3,4-cis isomer (0.27 g) were obtained.

Workup

  1. addition40 ml of saturated saline were added
  2. extractionfollowed by extraction with toluene
  3. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  4. concentrationthe extract was concentrated in an evaporator
  5. customThe 3,4-trans isomer (0.67 g) and the 3,4-cis isomer (0.27 g) were obtained

Sources & evidence

ORD record
ord-0384871485c14bc48ce62a1b862eeddd
Source dataset
uspto-grants-1992_07
Patent number
US05131947

Reaction notes

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