4-Chlorophenyl Isocyanate → HCID 73775312, compound

HRID 530635Notes

Reaction equation

HRID 530635 reaction equation
[F:1][C:2]([F:13])([F:12])[CH:3]([OH:11])[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>>[F:13][C:2]([F:1])([F:12])[CH:3]([O:11][C:22](=[O:23])[NH:21][C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1)[CH2:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 4422171HCID 4422171, compound

Product 1

HCID 73775312HCID 73775312, compoundYield 59.1%

Procedure

In a round bottomed reaction vessel, under argon, was placed 0.239 g (1.2 mmol) of 1,1,1-trifluoro-3-morpholin-4-yl-propan-2-ol and 0.203 g (1.3 mmol) of 4-chlorophenyl isocyanate. The vessel was capped, set in a bath at 85° C. and stirred. After 90 min, the mixture was cooled. The crude material was purified by chromatography on silica gel, eluting with hexanes-ethyl acetate (90:10), to give 0.250 g (59%) of (4-chloro-phenyl)-carbamic acid 2,2,2-trifluoro-1-morpholin-4-ylmethyl-ethyl ester as a white crystalline solid. (M+H)+=353 m/e.

Workup

  1. customIn a round bottomed reaction vessel, under argon, was placed
  2. customThe vessel was capped
  3. customset in a bath at 85° C.
  4. temperaturethe mixture was cooled
  5. customThe crude material was purified by chromatography on silica gel
  6. washeluting with hexanes-ethyl acetate (90:10)

Sources & evidence

ORD record
ord-b3856513cb7945b4b797f8f9779112de
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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