Thionyl Chloride → Ethyl (2-chloroethyl)-n-butylcarbamate

HRID 1648773Notes

Reaction equation

HRID 1648773 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:10][CH2:11][CH2:12][CH3:13])[C:5](=[O:9])[O:6][CH2:7][CH3:8].S(Cl)([Cl:16])=O>C(Cl)Cl>[Cl:16][CH2:2][CH2:3][N:4]([CH2:10][CH2:11][CH2:12][CH3:13])[C:5](=[O:9])[O:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54381911Ethyl (2-hydroxyethyl)-n-butylcarbamate

Product 1

HCID 12238083Ethyl (2-chloroethyl)-n-butylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

52 g of ethyl (2-hydroxyethyl)-n-butylcarbamate are placed in 125 ml of methylene chloride and treated dropwise with 41.6 g of thionyl chloride during 45 minutes at 20°-25° C. Then the mixture is allowed to react for an additional 1 hour at room temperature. After removing the solvent, the residue is distilled to yield pure ethyl (2-chloroethyl)-n-butylcarbamate; b.p. 91° C./0.07 Torr.

Workup

  1. customto react for an additional 1 hour at room temperature
  2. customAfter removing the solvent
  3. distillationthe residue is distilled

Sources & evidence

ORD record
ord-973f27da9d324ef5bd0f3d5e5b32d5cc
Source dataset
uspto-grants-1983_11
Patent number
US04413010

Reaction notes

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