Dichloromethane → HCID 14476476, compound

HRID 1492164Notes

Reaction equation

HRID 1492164 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])(=[O:3])[CH3:2].ClCCl.[CH3:15][C:16]([CH3:21])=[CH:17][C:18](Cl)=[O:19]>C(N(CC)CC)C>[C:1]([NH:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([NH:8][C:18](=[O:19])[CH:17]=[C:16]([CH3:21])[CH3:15])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7604m-AminoacetanilideHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 14476476HCID 14476476, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

56.7 g. ( 0.42 mole ) 3-acetamidoaniline in 400 ml. dichloromethane and 65 ml. ( 0.46 tool ) triethylamine are mixed, while cooling with ice, with 59.0 g. (0.46 mole) 3,3-dimethylacryloyl chloride and stirred for 2 hours at ambient temperature. The solution is thereafter extracted with water and the separated organic phase is dried over anhydrous sodium sulphate, evaporated and the residue mixed with ethyl acetate. Upon standing in a refrigerator, crystals separate out. Yield 45.7 g. (47% of theory); m.p. 144°-148° C.

Workup

  1. temperaturewhile cooling with ice, with 59.0 g
  2. extractionThe solution is thereafter extracted with water
  3. dry with materialthe separated organic phase is dried over anhydrous sodium sulphate
  4. customevaporated
  5. additionthe residue mixed with ethyl acetate
  6. customseparate out

Sources & evidence

ORD record
ord-63ae773b3cb74f3e97e5d7dbf6a30399
Source dataset
uspto-grants-1994_12
Patent number
US05373019

Reaction notes

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