Benzene → HCID 21481137, compound

HRID 435611Notes

Reaction equation

HRID 435611 reaction equation
C[C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9](O)[CH2:10][C:4]=2[CH:3]=1.[Cl-:18].[Ca+2].[Cl-].Cl.[CH:22]1C=CC=CC=1>>[Cl:18][CH:9]1[C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[S:6][C:5]2[CH:16]=[CH:17][CH:2]=[C:3]([CH3:22])[C:4]=2[CH2:10]1

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 5284359Calcium ChlorideHCID 11834917HCID 11834917, compound

Product 1

HCID 21481137HCID 21481137, compound

Procedure

10 g of 10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-ol, 100 ml of absolute benzene and 10 g of finely powdered calcium chloride are saturated at room temperature with dry hydrogen chloride gas (ca 2 hours) and then stirred for a further 20 hours. The calcium chloride is subsequently filtered off under a vacuum and washed with chloroform and the filtrate concentrated under reduced pressure. There is obtained 10-chloro-10,11-dihydro-methyl-dibenzo[b,f]thiepine as a yellow oil which crystallises on standing. 19.7 g of 10-chloro-10,11-dihydro-2-methyl-dibenzo-[b,f]thiepine dissolved in 100 ml of chloroform are heated under reflux for 24 hours together with 36.5 g of 1-carbethoxy-piperazine. Then the mixture is concentrated under reduced pressure and the residue crystallised from acetone/hexane. There is obtained 1-carbethoxy-4-(10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine of melting point 96°-98° C.

Workup

  1. filtrationThe calcium chloride is subsequently filtered off under a vacuum
  2. washwashed with chloroform
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-70fba09e0ce949308a13f754dfda5da5
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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