1,1,1,2-Tetrachloroethane → HCID 13154195, compound

HRID 1763640Notes

Reaction equation

HRID 1763640 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:7]1[CH:8]=[C:9]([C:22](Cl)=[O:23])[N:10]([CH:12]([Cl:21])[CH:13]([Cl:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)#[N:6].ClCC(Cl)(Cl)Cl>O>[C:5]([C:7]1[CH:8]=[C:9]2[N:10]([CH:11]=1)[CH:12]([Cl:21])[CH:13]([Cl:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:22]2=[O:23])#[N:6]

Participants

5

Reactant 3

HCID 124181,1,1,2-TetrachloroethaneHCID 6451240Aluminum(III) ChlorideHCID 13154194HCID 13154194, compound

Product 1

HCID 13154195HCID 13154195, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aluminum chloride (231 mg.) was added all at once to a mixture of 160 mg. of 4-cyano-N-(1,2-dichloro-2-phenylethyl)pyrrole-2-carbonyl chloride and 0.5 ml. of tetrachloroethane controlled at 140° C. After 4-5 minutes, the mixture is cooled, 15 ml. of water is added and the mixture is extracted with 4 × 10 ml. of chloroform. The extract is washed with water, dried and chromatographed on 10 g. of silica gel by elution with benzene:ethyl acetate (3:1 v/v). The first fraction provided 47 mg. (33%) of 2-cyano-5,6-dichloro-6,11-dihydro-5H-[2,1-b][3]benzazapin-11-one, m.p. 213°-223° C.

Workup

  1. additiononce to a mixture of 160 mg
  2. customcontrolled at 140° C
  3. temperaturethe mixture is cooled
  4. extractionthe mixture is extracted with 4 × 10 ml
  5. washThe extract is washed with water
  6. customdried
  7. customchromatographed on 10 g
  8. washof silica gel by elution with benzene:ethyl acetate (3:1 v/v)
  9. customThe first fraction provided 47 mg

Sources & evidence

ORD record
ord-126e515ccd4a4f178edd8c21ce6390dc
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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