Potassium Carbonate → Thiophene-2-carboxylic acid [4-(4-hydroxy-phenylsulfanyl)-3-nitro-phenyl]-amide

HRID 605252Notes

Reaction equation

HRID 605252 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+].[SH:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1>CN(C=O)C.O>[OH:32][C:29]1[CH:30]=[CH:31][C:26]([S:25][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)=[O:10])=[CH:4][C:3]=2[N+:16]([O-:18])=[O:17])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 771974N-(4-fluoro-3-nitrophenyl)thiophene-2-carboxamide

Product 1

HCID 67040141Thiophene-2-carboxylic acid [4-(4-hydroxy-phenylsulfanyl)-3-nitro-phenyl]-amideYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The product of Example 240a (1.50 g, 5.63 mmol) was dissolved in DMF to which K2CO3 (1.55 g, 11.27 mmol), and 4-mercapto-phenol (711 mg, 5.634 mmol) were added. The reaction mixture was then heated to 80° C. for 2 hrs. At this point the reaction mixture was cooled to room temperature and diluted with water which was then extracted with ethyl acetate to isolate the desired compound (1.66 g, 79%).

Workup

  1. additionwere added
  2. temperatureAt this point the reaction mixture was cooled to room temperature
  3. extractionwas then extracted with ethyl acetate

Sources & evidence

ORD record
ord-b46682478ecc4bb4998f7aad4c465cc0
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…