Phosgene → Thiomorpholine-4-carbonyl chloride

HRID 1291761Notes

Reaction equation

HRID 1291761 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[C:7](Cl)([Cl:9])=[O:8]>C1(C)C=CC=CC=1>[N:1]1([C:7]([Cl:9])=[O:8])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 67164Thiomorpholine

Product 1

HCID 19080217Thiomorpholine-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 10 g (97 mmol) of thiomorpholine in 200 ml of toluene is added dropwise at 0° to a solution of 85 ml (165 mmol) of 20% phosgene in toluene and the white suspension is stirred for 1 h at RT. Excess phosgene is driven off by introducing nitrogen, the suspension is filtered, and the filtrate is concentrated by evaporation. The title compound is obtained in the form of a yellow oil. IR (CH2Cl2, cm-1): 1735, 1450, 1440, 1405, 1370, 1290, 1180.

Workup

  1. additionby introducing nitrogen
  2. filtrationthe suspension is filtered
  3. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-c580a4603e7c4806b30536f8fab50c42
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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