Acetic Acid → HCID 69738282, compound

HRID 498134Notes

Reaction equation

HRID 498134 reaction equation
[CH:1]([N:4]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[C:5](=[O:10])[CH2:6][C:7](=O)[CH3:8])([CH3:3])[CH3:2].C(O)(=O)C.[NH3:28]>C(OCC)(=O)C>[CH:1]([N:4]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[C:5](=[O:10])/[CH:6]=[C:7](\[NH2:28])/[CH3:8])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 222Ammonia2×HCID 22320826HCID 22320826, compound

Product 1

HCID 69738282HCID 69738282, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

N-Isopropyl-3-oxo-N-[4-(phenylamino)phenyl]-butyramide (30.0 g, 0.0967 mol) and conc. acetic acid (1.4 g, 0.0233 mol) in ethyl acetate (140 g) were introduced into an autoclave. Ammonia (16.0 g, 0.9395 mol) was introduced in the course of 10 minutes and the temp. of the reaction mixture was increased to 35° C. during this period. After the introduction a pressure of 14 bar is present. The temperature of the reaction mixture was heated to 70° C. in the course of 30 min. In the course of this, the pressure rose to 17 bar. After 2.5 h under these conditions, the reaction mixture was cooled to 25° C. and ammonia was released. The reaction mixture was further cooled to 5° C. in order to crystallize the product. The suspension was filtered. The pale grey solid was washed with cold (0° C.) ethyl acetate (20 ml) and dried in vacuo (50 mbar) at 35° C. for 2 days. (Z)-3-Aminobut-2-enoic acid N-isopropyl-N-[4-(phenylamino)phenyl]amide (27.2 g, 91.0%) was obtained.

Workup

  1. temperatureThe temperature of the reaction mixture was heated to 70° C. in the course of 30 min
  2. temperaturethe reaction mixture was cooled to 25° C.
  3. temperatureThe reaction mixture was further cooled to 5° C. in order
  4. customto crystallize the product
  5. filtrationThe suspension was filtered
  6. washThe pale grey solid was washed with cold (0° C.) ethyl acetate (20 ml)
  7. customdried in vacuo (50 mbar) at 35° C. for 2 days

Sources & evidence

ORD record
ord-19987aa9a0d94978ab4e6079192bf7a6
Source dataset
uspto-grants-2005_09
Patent number
US06949677B2

Reaction notes

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