Ammonia → HCID 54243497, compound

HRID 1704709Notes

Reaction equation

HRID 1704709 reaction equation
C([N:3](CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][C:21]=1[Cl:22])[C:12]([CH:14]=[CH:15][C:16](O)=[O:17])=[O:13].ClC(OCC)=O.N>C(Cl)(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([C:12](=[O:13])[CH:14]=[CH:15][C:16]([NH2:3])=[O:17])[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 3067241HCID 3067241, compound

Product 1

HCID 54243497HCID 54243497, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

28 ml of triethylamine was dissolved in 600 ml of chloroform, then 49g of 3-(3,4-dichlorobenzoyl)acrylic acid was added. The resulting solution was cooled to 0° C., and 42g of ethyl cloroformate was added. The mixture was warmed to 20° C., stirred for one hour, cooled to 0° C. and then held there while gaseous ammonia was passed into the solution until no further heat of reaction was noted. A precipitate that formed was collected, washed with water and then with acetone to give 4-(3,4-dichlorophenyl)-4-oxo-2-butenamide (4A), as a white solid, m.p.: 208° C. (with decomposition).

Workup

  1. temperatureThe mixture was warmed to 20° C.
  2. temperaturecooled to 0° C.
  3. temperatureno further heat of reaction
  4. customA precipitate that formed
  5. customwas collected
  6. washwashed with water

Sources & evidence

ORD record
ord-23c3b7d485c24caeaadd2222da769a81
Source dataset
uspto-grants-1978_11
Patent number
US04127656

Reaction notes

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