Methyl chloroformate → Methyl (1,1-dimethylethyl)-(3,3,3-trichloro-2-hydroxypropyl)carbamate

HRID 127955Notes

Reaction equation

HRID 127955 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH:7]([OH:12])[C:8]([Cl:11])([Cl:10])[Cl:9])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:20][O:21][C:22](Cl)=[O:23]>ClCCl>[CH3:4][C:2]([N:5]([CH2:6][CH:7]([OH:12])[C:8]([Cl:11])([Cl:10])[Cl:9])[C:22](=[O:23])[O:21][CH3:20])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 234710203-(Tert-butylamino)-1,1,1-trichloropropan-2-ol

Product 1

HCID 54278558Methyl (1,1-dimethylethyl)-(3,3,3-trichloro-2-hydroxypropyl)carbamateYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5 grams of 3-(1,1-dimethylethylamino)-1,1,1-trichloro-2-propanol and 2.15 grams of triethylamine in 50 grams of dichloromethane, cooled to -60° C., 2.01 grams of methylchloroformate was added dropwise during 5 minutes. After allowing the reaction mixture to warm to ambient temperature during 1 hour, the mixture was stirred for 3 hours. The reaction mixture was evaporated under a reduced pressure of 100 mm. Hg to 5.6 grams of an oil which was crystallized from 50 grams of hexane to yield 5.2 grams of white methyl (1,1-dimethylethyl)-(3,3,3-trichloro-2-hydroxypropyl)carbamate melting 100°-101° C.

Workup

  1. customThe reaction mixture was evaporated under a reduced pressure of 100 mm. Hg to 5.6 grams of an oil which
  2. customwas crystallized from 50 grams of hexane

Sources & evidence

ORD record
ord-29a047cf61934b129d817411fe33fe77
Source dataset
uspto-grants-1981_03
Patent number
US04258060

Reaction notes

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