Dichloromethane → HCID 21278866, compound

HRID 2291584Notes

Reaction equation

HRID 2291584 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][N:17]([NH2:20])[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].ClCCl.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>O1CCOCC1>[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][N:17]([NH:20][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:18][CH2:19]3)=[O:13])[C:6]=2[CH:21]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 212788513-[2-(4-Aminopiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2(3H)-one

Product 1

HCID 21278866HCID 21278866, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-chloro-3-[(4-amino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (0.85 g), anhydrous potassium carbonate (430 mg), dichloromethane (40 ml), dioxane (10 ml) and ethyl chloroformate (339 mg) was stirred for 1.5 hours at room temperature. The insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The residue was recrystallized from a mixture of chloroform and dioxane to give colorless crystals of 5-chloro-3-[(4-ethoxycarbonylamino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (0.35 g).

Workup

  1. filtrationThe insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from a mixture of chloroform and dioxane

Sources & evidence

ORD record
ord-64b4d959debc4b35ab29c9831f5cb0cd
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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