Thionyl Chloride → N-chloromethylcarbamic acid 3-chlorophenyl ester

HRID 372347Notes

Reaction equation

HRID 372347 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([O:12][C:13](=[O:18])[NH:14][CH2:15]OC)[CH:9]=[CH:10][CH:11]=1>C(Cl)(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([O:12][C:13](=[O:18])[NH:14][CH2:15][Cl:3])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54102306HCID 54102306, compound

Product 1

HCID 54201978N-chloromethylcarbamic acid 3-chlorophenyl esterYield 70.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

62 ml (0.85 mole) of thionyl chloride were added to 167 g (0.775 mole) of N-methoxymethylcarbamic acid 3-chlorophenyl ester in 200 ml of carbon tetrachloride. After the evolution of gas had ceased, the mixture was cooled to 0° C, while keeping the reaction mixture stirrable by adding carbon tetrachloride. The precipitate which had separated out was filtered off, rinsed with cold carbon tetrachloride and dried in vacuo at 40° C. 119.5 g (70% of theory) of N-chloromethylcarbamic acid 3-chlorophenyl ester of melting point 90° C were obtained.

Workup

  1. customThe precipitate which had separated out
  2. filtrationwas filtered off
  3. washrinsed with cold carbon tetrachloride
  4. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-977f9a66926445e3b8f828569baf106f
Source dataset
uspto-grants-1978_05
Patent number
US04090862

Reaction notes

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