Hydrochloric Acid → HCID 19887198, compound

HRID 654405Notes

Reaction equation

HRID 654405 reaction equation
[CH2:1]([N:5]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[C:6](=[O:16])[CH:7](Br)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[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.Cl>C1(C)C=CC=CC=1>[CH2:3]([CH:2]1[CH2:1][N:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[C:6](=[O:16])[CH:7]1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 54384673HCID 54384673, compound

Product 1

HCID 19887198HCID 19887198, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(2-Butenyl)-N-(3-trifluoromethylphenyl)-2-bromo-2-(4-fluorophenyl)acetamide (1.9 g) was added to 20 ml of toluene, followed by the addition of 1.2 ml of tributyltin hydride and an extremely small amount of α,α-azobisisobutyronitrile (AIBN) under stirring at 70° C. After the reaction mixture was continuously stirred for 1 hour, 60 ml of 20% hydrochloric acid were added, followed by extraction with toluene. After the extract was dried over anhydrous sodium sulfate, the extract was concentrated in an evaporator and then subjected to chromatography on a silica gel column. The 3,4-trans isomer (0.9 g) and the 3,4-cis isomer (0.27 g) were obtained.

Workup

  1. extractionfollowed by extraction with toluene
  2. dry with materialAfter the extract was dried over anhydrous sodium sulfate
  3. concentrationthe extract was concentrated in an evaporator
  4. customThe 3,4-trans isomer (0.9 g) and the 3,4-cis isomer (0.27 g) were obtained

Sources & evidence

ORD record
ord-d8674251df924b0696e4aabcf1c06905
Source dataset
uspto-grants-1992_07
Patent number
US05131947

Reaction notes

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