4-Chlorophenyl Isocyanate → HCID 53874791, compound

HRID 374491Notes

Reaction equation

HRID 374491 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[O:17])=[CH:11][CH:10]=1.[CH2:18]1[O:20][CH:19]1[CH2:21][OH:22]>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]([CH2:21][OH:22])[CH2:18][O:20][C:16]2=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 11164Glycidol

Product 1

HCID 53874791HCID 53874791, compoundYield 143%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 8.5 ml quantity of triethylamine was added dropwise to a dichloromethane (25 ml) solution of 2.5 g of 4-chlorophenyl isocyanate and 2.5 g of glycidol at 40° C., and the mixture was stirred at the same temperature for 20 hours. The reaction mixture was washed with 5% hydrochloric acid, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified by dichloromethane-ethanol gradient elution to give 5.30 g of the title compound as an oil (yield 69%).

Workup

  1. washThe reaction mixture was washed with 5% hydrochloric acid
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by dichloromethane-ethanol gradient elution

Sources & evidence

ORD record
ord-4f9e2ac39fce458d9327d5481026d202
Source dataset
uspto-grants-1996_01
Patent number
US05480899

Reaction notes

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