Ethyl chloroformate → HCID 14648418, compound

HRID 1638287Notes

Reaction equation

HRID 1638287 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:21]=1.[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:15][CH2:16][CH:17]([O:20][C:22]([O:23][CH2:24][CH3:25])=[O:26])[CH2:18][CH2:19]3)=[O:13])[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 3082453Hpr 611

Product 1

HCID 14648418HCID 14648418, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

5-Chloro-3-(4-hydroxypiperidinocarbonylmethyl)benzothiazolin-2-one (3.2 g) was dissolved in dry pyridine (15 ml) and the solution was cooled. After ethyl chlorocarbonate (1.5 g) was dropwise added to the solution, the resultant was stirred for 8 hours at 80° C. Pyridine was evaporated off under vacuum from the reaction mixture and the residue was recrystallized from a mixture of chloroform and ethanol to yield the title compound as colorless crystals (3.2 g). mp 196°-197° C.

Workup

  1. temperaturethe solution was cooled
  2. customPyridine was evaporated off under vacuum from the reaction mixture
  3. customthe residue was recrystallized from a mixture of chloroform and ethanol

Sources & evidence

ORD record
ord-ae96f7b61a1f4a558cf91b40802ca34e
Source dataset
uspto-grants-1989_11
Patent number
US04879301

Reaction notes

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