Ethyl chloroformate → HCID 19004094, compound

HRID 2225364Notes

Reaction equation

HRID 2225364 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=[C:7]([N:16]3[CH2:21][CH2:20][N:19](C)[CH2:18][CH2:17]3)[C:6]=2[CH:23]=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=[C:7]([N:16]3[CH2:21][CH2:20][N:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:18][CH2:17]3)[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 16351ClothiapineHCID 516892Sodium Bicarbonate

Product 1

HCID 19004094HCID 19004094, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.86 g of 2-chloro-11-(4-methyl-1-piperazinyl)dibenzo[b,f][1,4]thiazepine and 0.81 g of ethyl chloroformate in 5 ml of toluene was refluxed for 5 hrs. Ice water was added to the reaction mixture and made alkaline with sodium bicarbonate. The mixture was extracted with methylene chloride and the methylene chloride layer was washed with water, dried and concentrated. The residue was chromatographed on silica gel using methylene chloride as an eluent to give 0.70 g of colorless crystals, which were recrystallized from a mixture of isopropyl ether and n-pentane to give colorless prisms, mp 96.5°-97.5° C.

Workup

  1. temperaturewas refluxed for 5 hrs
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe methylene chloride layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-813f9eac5f4e40d5b90b26619ca67fb3
Source dataset
uspto-grants-1994_09
Patent number
US05344828

Reaction notes

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