Ammonium Chloride → 2-Anilino-5-phenylthiophene-3-carboxamide

HRID 1967158Notes

Reaction equation

HRID 1967158 reaction equation
[NH:1]([C:8]1[S:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:12]=1[C:13](O)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C([N:27](CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].O>[NH:1]([C:8]1[S:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:12]=1[C:13]([NH2:27])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 582564742-Anilino-5-phenylthiophene-3-carboxylic acid

Product 1

HCID 446103702-Anilino-5-phenylthiophene-3-carboxamide

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-anilino-5-phenylthiophene-3-carboxylic acid (47.3 mg, 0.160 mmol), ammonium chloride (17.12 mg, 0.320 mmol), and N,N-diisopropylethylamine (0.084 ml, 0.480 mmol) in N,N-dimethylformamide (1 mL) was added 1-hydroxybenzotriazole hydrate (32.4 mg, 0.240 mmol) and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (46.0 mg, 0.240 mmol). After being stirred for 15 hours, the reaction mixture was diluted with ethyl acetate (20 mL), saturated aqueous sodium bicarbonate solution (10 mL), and water (2 mL). The layers were separated and the organic layer was washed with water (2×5 mL) and brine (10 mL), dried over sodium sulfate, filtered, and concentrated. The crude reaction mixture was purified by silica gel chromatography (50% ethyl acetate/hexanes) to afford 2-anilino-5-phenylthiophene-3-carboxamide.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water (2×5 mL) and brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude reaction mixture
  7. customwas purified by silica gel chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-89ad3c9d686d418d836f40f4c8209cbc
Source dataset
uspto-grants-2013_04
Patent number
US08420695B2

Reaction notes

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