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

HRID 364973Notes

Reaction equation

HRID 364973 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>[CH2:7]([O:6][C:5](=[O:9])[N:4]([CH2:3][CH2:2][Cl:16])[CH2:10][CH2:11][CH2:12][CH3:13])[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-64b24735ca3245dba024abbeef7ee7db
Source dataset
uspto-grants-1986_08
Patent number
US04607051

Reaction notes

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