2-Chlorobenzoyl isocyanate → HCID 13772933, compound

HRID 980570Notes

Reaction equation

HRID 980570 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:23])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH2:5].[Cl:24][C:25]1[CH:35]=[CH:34][CH:33]=[CH:32][C:26]=1[C:27]([N:29]=[C:30]=[O:31])=[O:28]>C1(C)C=CC=CC=1>[Cl:24][C:25]1[CH:35]=[CH:34][CH:33]=[CH:32][C:26]=1[C:27]([NH:29][C:30]([NH:5][C:4]1[CH:3]=[C:2]([Cl:1])[C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:7]([Cl:23])[CH:6]=1)=[O:31])=[O:28]

Participants

4

Reactant 2

HCID 99423112-Chlorobenzoyl isocyanateHCID 13772932HCID 13772932, compound

Product 1

HCID 13772933HCID 13772933, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution containing 1.55 grams (0.004 moles) of 3,5-dichloro-4-(2-phenylphenylmethoxy) aniline prepared in Part B and 5 milliliters of toluene, which solution was heated to a temperature of 60° C. and placed under an atmosphere of nitrogen, was added 0.98 grams (0.005 moles) of 2-chlorobenzoyl isocyanate. The resulting mixture was maintained at a temperature of 60° C. for a period of 0.5-1.0 hours. After cooling to ambient temperature, the reaction mixture was diluted with 1 milliliter of toluene. This mixture was then filtered to give a solid material. The solid material was washed once with toluene, once with a toluene-hexane mixture (1:1 volume ratio) and finally once with hexane and then dried overnight in a vacuum oven at 50° C. This afforded a white powder material having a melting point of 188.5° C.-192.0° C. Elemental analysis of the white powder indicated the following:

Workup

  1. temperatureThe resulting mixture was maintained at a temperature of 60° C. for a period of 0.5-1.0 hours
  2. temperatureAfter cooling to ambient temperature
  3. filtrationThis mixture was then filtered
  4. customto give a solid material
  5. washThe solid material was washed once with toluene, once with a toluene-hexane mixture (1:1 volume ratio) and finally once with hexane
  6. customdried overnight in a vacuum oven at 50° C
  7. customThis afforded a white powder material

Sources & evidence

ORD record
ord-ff714219c2284c29a24e6f8247c7516e
Source dataset
uspto-grants-1987_01
Patent number
US04638088

Reaction notes

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