N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamide → HCID 20280389, compound

HRID 1247972Notes

Reaction equation

HRID 1247972 reaction equation
[NH2:1][C:2]1[C:6]([C:7](=O)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][NH:4][N:3]=1.CN(C)[CH:17]=[CH:18][C:19]([C:21]1[CH:22]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:24]=[CH:25][CH:26]=1)=O>C(O)(=O)C>[CH2:7]([C:6]1[CH:5]=[N:4][N:3]2[C:19]([C:21]3[CH:22]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:24]=[CH:25][CH:26]=3)=[CH:18][CH:17]=[N:1][C:2]=12)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamideHCID 178509267HCID 178509267, compound

Product 1

HCID 20280389HCID 20280389, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.87 g of 3-amino-4-benzoylpyrazole and 2.32 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide (Example 168) in 50 ml of glacial acetic acid was refluxed for 8 hours. The reaction mixture was evaporated to dryness and a saturated sodium bicarbonate solution was added along with 400 ml of methylene chloride. The solid that separated was recovered by filtration and was the desired compound (2.57 g, mp 205°-207° C.). The methylene chloride solution afforded more compound (0.73 g, mp 205°-207° C.).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additiona saturated sodium bicarbonate solution was added along with 400 ml of methylene chloride
  3. customThe solid that separated
  4. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-7db7d28bd2d545b0a2469452699f3a83
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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