N,N-Dimethylaniline → Cyclopentylmethyl carbonochloridate

HRID 280872Notes

Reaction equation

HRID 280872 reaction equation
CN(C)C1C=CC=CC=1.[CH:10]1([CH2:15][OH:16])[CH2:14][CH2:13][CH2:12][CH2:11]1.[C:17](Cl)([Cl:19])=[O:18].C1(C)C=CC=CC=1>>[Cl:19][C:17]([O:16][CH2:15][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:18]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 1140TolueneHCID 6371PhosgeneHCID 77195Cyclopentanemethanol

Product 1

HCID 13077898Cyclopentylmethyl carbonochloridateYield 81%

Procedure

A mixture of 24.2 g (0.20 mole) N,N-dimethylaniline and 20.3 g (0.20 mole) of cyclopentylmethanol was slowly added to a 20% solution of phosgene in toluene (104 ml, 0.20 mole) cooled to -5° to +5° C. After the addition the reaction mixture was allowed to attain room temperature and was kept at room temperature for 30 min. The precipitate was filtered off and the solvent was evaporated. Distillation in vacuo gave 26.3 g (81%) of cyclopentylmethyl chloroformate. Bp17-20 82°-84° C., nD21 1.4541. Analysis for C7H11ClO2. Found (calculated): Cl 21.37 (21.80). IR (neat) cm-1 : 1790 (CO).

Workup

  1. temperaturecooled to -5° to +5° C
  2. additionAfter the addition the reaction mixture
  3. customto attain room temperature
  4. filtrationThe precipitate was filtered off
  5. customthe solvent was evaporated
  6. distillationDistillation in vacuo

Sources & evidence

ORD record
ord-d1d9f2a4364c4edc898d7829f8bbff19
Source dataset
uspto-grants-1986_05
Patent number
US04591583

Reaction notes

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