Triethylamine → HCID 21513023, compound

HRID 1575998Notes

Reaction equation

HRID 1575998 reaction equation
C(OCC)(=O)C.[OH:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=1)[NH:11][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14].[CH3:20][C:21]([N:28]=[C:29]=[O:30])([CH3:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24].C(N(CC)CC)C>CCCCCC.C1C=CC=CC=1>[CH3:27][C:21]([NH:28][C:29]([O:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=1)[NH:11][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14])=[O:30])([CH3:20])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 4074981,1,3,3-Tetramethylbutyl isocyanateHCID 21225962HCID 21225962, compound

Product 1

HCID 21513023HCID 21513023, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Conditions

Temperature
-15 °C

Procedure

A reaction vessel is charged with 100 parts of ethyl acetate, 17.7 parts of 3'-hydroxy-2-methylacrylanilide, 23.3 parts of 1,1,3,3-tetramethylbutyl isocyanate and 4 parts of triethylamine. The reaction mixture is heated at reflux for about 18 hours with stirring, and then 100 parts of benzene and 50 parts of hexane are added. The reaction mixture is cooled to -15°C and filtered. The solids are washed with hexane and recrystallized from aqueous alcohol to give 12.5 parts of 3'-(1,1,3,3-tetramethylbutylcarbamoyloxy)-2-methylacrylanilide, m.p. 118°-120°C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for about 18 hours
  3. filtrationfiltered
  4. washThe solids are washed with hexane
  5. customrecrystallized from aqueous alcohol

Sources & evidence

ORD record
ord-09568676b3844ce1a2ecd129b0ea6d0a
Source dataset
uspto-grants-1976_09
Patent number
US03979202

Reaction notes

Loading…