3'-Aminoacetophenone → HCID 4054491, compound

HRID 1167829Notes

Reaction equation

HRID 1167829 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=1.[CH3:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1)=[O:18].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C.CN(C=O)C>[C:17]([C:19]1[CH:20]=[C:21]([NH:25][C:13]([C:11]2[S:12][C:8]([Cl:7])=[CH:9][CH:10]=2)=[O:15])[CH:22]=[CH:23][CH:24]=1)(=[O:18])[CH3:16]

Participants

8

Reactant 4

HCID 74173'-AminoacetophenoneHCID 8471TriethylamineHCID 65578Oxalyl chloride2×HCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 4054491HCID 4054491, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Oxalyl chloride (4.9 mL, 56.00 mmol) was added to solution of 5-chloro-thiophene-2-carboxylic acid (4.78 g, 29.40 mmol), DMF (0.25 mL), and CH2Cl2 (50 ml) at room temperature. After stirring overnight, the reaction was stripped of solvent and unreacted oxalyl choride in vacuo, giving a colorless oil. The oil was dissolved in CH2Cl2 (50 mL), and treated with 3-aminoacetophenone (3.78 g, 28.00 mmol) and triethylamine (4.68 mL, 33.60 mmol). After stirring for 1 h, the mixture was diluted with 800 mL of ethyl acetate, extracted with 1N HCl, 1N NaHCO3, brine, and dried over MgSO4. The resulting solution was concentrated in vacuo to a volume of 100 mL, giving 5-chloro-thiophene-2-carboxylic acid (3-acetyl-phenyl)-amide as a white powder, which was collected by filtration and dried under high vacuum (8.12 g, 81% yield).

Workup

  1. customgiving a colorless oil
  2. stirringAfter stirring for 1 h
  3. extractionextracted with 1N HCl, 1N NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationThe resulting solution was concentrated in vacuo to a volume of 100 mL

Sources & evidence

ORD record
ord-ac1e8753548a47fc879c348d71a688ba
Source dataset
uspto-grants-2003_09
Patent number
US06620828B2

Reaction notes

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