Hydrochloric Acid → chloromethyl N,N-di-n-butylcarbamate

HRID 2246145Notes

Reaction equation

HRID 2246145 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].C(N(CC)CC)C.[CH2:14]([NH:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].Cl>COC1CCCC1>[CH2:14]([N:18]([CH2:19][CH2:20][CH2:21][CH3:22])[C:2](=[O:3])[O:4][CH2:5][Cl:6])[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8148DibutylamineHCID 8471TriethylamineHCID 62754Chloromethyl chloroformate

Product 1

HCID 86609817chloromethyl N,N-di-n-butylcarbamate

Reagents, catalysts & solvents 1

HCID 138539Cyclopentyl methyl etherSolvent

Procedure

Chloromethyl chloroformate (5.0 ml) was added dropwise to 100 ml of a solution of 11.7 ml of triethylamine and 11.3 ml of N,N-di-n-butylamine in cyclopentyl methyl ether under ice cooling, and the mixture was stirred at room temperature for 13 hr. 2 N hydrochloric acid (100 ml) was added thereto, followed by separation. The organic layer was washed with 100 ml of a 5% aqueous sodium hydrogencarbonate solution and 100 ml of semi-saturated brine, was dried over anhydrous magnesium sulfate, and was filtered, and the solvent was removed by distillation under the reduced pressure to give 12.7 g of chloromethyl N,N-di-n-butylcarbamate.

Workup

  1. customfollowed by separation
  2. washThe organic layer was washed with 100 ml of a 5% aqueous sodium hydrogencarbonate solution and 100 ml of semi-saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. customthe solvent was removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-210884fc200a41b5b4a0351664bf581c
Source dataset
uspto-grants-2010_03
Patent number
US07687490B2

Reaction notes

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