1-(5-(4-Bromophenyl)-4-hydroxythiophen-3-YL)ethan-1-one → HCID 73224890, compound

HRID 2425954Notes

Reaction equation

HRID 2425954 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:14]([CH3:16])=O)[C:12]=2[OH:13])=[CH:4][CH:3]=1.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][NH:23][C:24]([C:26]1[S:27][C:28]([C:31]([NH:33][NH2:34])=[O:32])=[CH:29][CH:30]=1)=[O:25]>CC(O)C>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][NH:23][C:24]([C:26]1[S:27][C:28]([C:31]([NH:33][N:34]=[C:14]([C:11]2[C:12]([OH:13])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[S:9][CH:10]=2)[CH3:16])=[O:32])=[CH:29][CH:30]=1)=[O:25]

Participants

4

Reactant 2

HCID 442072901-(5-(4-Bromophenyl)-4-hydroxythiophen-3-YL)ethan-1-oneHCID 57688120HCID 57688120, compound

Product 1

HCID 73224890HCID 73224890, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-(4-Bromophenyl)-3-hydroxy-4-methylcarbonylthiophene (50.1 mg, 0.17 mmol) and 5-hydrazinocarbonylthiophene-2-carboxylic acid (furan-2-ylmethyl)amide (45.0 mg, 0.17 mmol) prepared in Reference Synthetic Example 13 in 2-propanol (4.0 mL) were heated with p-tosylic acid monohydrate (6 mg) at 100° C. for 7.5 hours and cooled to room temperature. The precipitated solid was recovered by filtration, washed with 2-propanol (1 mL) and dried to give the desired product (yield 72%).

Workup

  1. filtrationThe precipitated solid was recovered by filtration
  2. washwashed with 2-propanol (1 mL)
  3. customdried

Sources & evidence

ORD record
ord-eddb01e00c264df4b2531801955a230a
Source dataset
uspto-grants-2011_06
Patent number
US07968542B2

Reaction notes

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