Triethylamine → 2,2,2-Trichloroethyl (2-chloroethyl)carbamate

HRID 1439761Notes

Reaction equation

HRID 1439761 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][Cl:5].Cl[C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8].C(N(CC)CC)C>CN(C)C=O.O>[Cl:5][CH2:4][CH2:3][NH:2][C:7](=[O:8])[O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 3319082,2,2-Trichloroethyl (2-chloroethyl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

One mole of 1-amino-2-chloroethane hydrochloride in 500 ml of dimethylformamide at 0° C is treated with 1 mole of β,β,β-trichloroethyl chloroformate after which a solution of 2 moles of triethylamine in 200 ml of dimethylformamide is slowly added. Upon completion of the addition, the reaction is diluted with 2 liters of water and extracted twice with 750 ml of ether. The ether extracts are washed twice with 500 ml of water then twice with 500 ml of 1 M HCl, dried over sodium sulfate and evaporated to dryness to give β,β,β-trichloroethyl N-(2-chloroethyl)carbamate.

Workup

  1. additionis slowly added
  2. additionUpon completion of the addition
  3. extractionextracted twice with 750 ml of ether
  4. washThe ether extracts are washed twice with 500 ml of water
  5. dry with materialtwice with 500 ml of 1 M HCl, dried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-21acdb0e03af464c95528d2ba2c9976f
Source dataset
uspto-grants-1977_11
Patent number
US04060630

Reaction notes

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