3,4-Dichlorophenyl isocyanate → HCID 21513034, compound

HRID 1576001Notes

Reaction equation

HRID 1576001 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[NH:5][C:6](=[O:10])/[CH:7]=[CH:8]/[CH3:9].[Cl:14][C:15]1[CH:16]=[C:17]([N:22]=[C:23]=[O:24])[CH:18]=[CH:19][C:20]=1[Cl:21].C(N(CC)CC)C>C(OCC)(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([NH:22][C:23]([O:1][C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=2)[NH:5][C:6](=[O:10])/[CH:7]=[CH:8]/[CH3:9])=[O:24])[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 8471TriethylamineHCID 6055750NSC222527

Product 1

HCID 21513034HCID 21513034, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
55 °C

Procedure

A reaction vessel is charged with 100 parts of ethyl acetate, 17.7 parts of 3'-hydroxycrotonanilide and 18.8 parts of 3,4-dichlorophenyl isocyanate. The reaction mixture is heated to about 55°C and one part of triethylamine is added. An additional 100 parts of ethyl acetate is added and the reaction mixture heated at reflux for about one-half hour, cooled and filtered. The solids are washed with ethyl acetate and air dried to give 31 parts of 3'-(3,4-dichlorophenylcarbamoyloxy)crotonanilide, m.p. 193°-194°C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for about one-half hour
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe solids are washed with ethyl acetate and air
  6. customdried

Sources & evidence

ORD record
ord-dc31dd115d9f49a0b64919f8b38a88d8
Source dataset
uspto-grants-1976_09
Patent number
US03979202

Reaction notes

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