Hydrochloric Acid → 6,11-Dihydro-11-oxo-dibenzo[b,e]thiepine-2-acetic acid

HRID 268038Notes

Reaction equation

HRID 268038 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13](=C=O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2Cl)=[CH:8][CH:7]=1)C.[Cl-].[Al+3].[Cl-].[Cl-].Cl.C[CH2:30][O:31]CC>[N+](C1C=CC=CC=1)([O-])=O>[O:31]=[C:30]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][S:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:3])=[O:23])=[CH:7][C:8]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6451240Aluminum(III) ChlorideHCID 1317101004-(2-Chloro-carbonyl-benzyl-thio)phenylacetic acid ethyl ester

Product 1

HCID 123300366,11-Dihydro-11-oxo-dibenzo[b,e]thiepine-2-acetic acid

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

7.0 g of 4-(2-chloro-carbonyl-benzyl-thio)phenylacetic acid ethyl ester are dissolved in 30 cc of nitrobenzene and this solution is added dropwise, at room temperature, to a solution of 3.32 g of aluminium chloride in 50 cc of nitrobenzene. The resulting red solution is then heated in an oil bath of 100° for 3 hours. The reaction solution is subsequently poured on a mixture of ice and 10 N hydrochloric acid, is diluted with ether, and the organic phase is separated, washed with water, dried with sodium sulphate, purified with charcoal and filtered. The solvent is completely removed at reduced pressure and the oily residue is dissolved in ether, the ether phase is washed with a 10% sodium bicarbonate solution and then with water, is dried with sodium sulphate, filtered, and the solvent is removed by distillation at reduced pressure. 6,11-Dihydro-11-oxo-dibenzo[b,e]thiepine-2-acetic acid ethyl ester crystallizes from ether/pentane. M.P. 96°-97°.

Workup

  1. temperatureThe resulting red solution is then heated in an oil bath of 100° for 3 hours
  2. customthe organic phase is separated
  3. washwashed with water
  4. dry with materialdried with sodium sulphate
  5. custompurified with charcoal
  6. filtrationfiltered
  7. customThe solvent is completely removed at reduced pressure
  8. dissolutionthe oily residue is dissolved in ether
  9. washthe ether phase is washed with a 10% sodium bicarbonate solution
  10. dry with materialwith water, is dried with sodium sulphate
  11. filtrationfiltered
  12. customthe solvent is removed by distillation at reduced pressure
  13. custom6,11-Dihydro-11-oxo-dibenzo[b,e]thiepine-2-acetic acid ethyl ester crystallizes from ether/pentane

Sources & evidence

ORD record
ord-a7cd4e42c0694844aa4f51a07a6c1f78
Source dataset
uspto-grants-1976_03
Patent number
US03946036

Reaction notes

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