1,1-Dichloroethane → HCID 13151868, compound

HRID 485449Notes

Reaction equation

HRID 485449 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](OC(=O)C)(=[O:7])[CH3:6].ClC(Cl)C.[C:16]([C:18]1[CH:19]=[CH:20][C:21]2[CH2:27][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[S:23][C:22]=2[CH:32]=1)#[N:17]>>[C:5]([C:29]1[CH:30]=[CH:31][C:24]2[S:23][C:22]3[CH:32]=[C:18]([C:16]#[N:17])[CH:19]=[CH:20][C:21]=3[CH2:27][CH2:26][C:25]=2[CH:28]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 7918Acetic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 13490401HCID 13490401, compound

Product 1

HCID 13151868HCID 13151868, compound

Procedure

Add 125.5 g. (0.94 mole) of aluminum chloride and 47.9 g. (0.47 mole) of acetic anhydride to 1.01 of dichloroethane. Stir at room temperature for 10 minutes. Add 14 g. (0.058 mole) of 3-cyano-10,11-dihydrodibenzo[b,f]thiepin in portions. Stir at room temperature for 4 hours. Pour the reaction mixture over ice and extract into ethyl acetate. Wash with water, dry over sodium sulfate, filter and evaporate to dryness to obtain the title product. (m.p. 138°-141° C.)

Workup

  1. additionAdd 125.5 g
  2. additionAdd 14 g
  3. stirringStir at room temperature for 4 hours
  4. additionPour the reaction mixture over ice
  5. extractionextract into ethyl acetate
  6. washWash with water
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. customevaporate to dryness

Sources & evidence

ORD record
ord-9e86d9b3053f47d0a3ab372335167374
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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