Nitrogen → HCID 20775752, compound

HRID 2193917Notes

Reaction equation

HRID 2193917 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:10][C:11]=1[NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])=[O:6].N#N.Cl[C:32]1[CH:40]=[C:39](Cl)[CH:38]=[CH:37][C:33]=1C(Cl)=O>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:10][C:11]=1[N:12]([C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])[C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:33]=1)=[O:6]

Participants

6

Reactant 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 666452,4-Dichlorobenzoyl chlorideHCID 20775751HCID 20775751, compound

Product 1

HCID 20775752HCID 20775752, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium Hydride (60% dispersion in oil, 80 mg, 1.5 mmol) was added to an ice-cold solution 5-Phenyl-3-phenylamino-thiophene-2-carboxylic acid methyl ester (2) (230 mg, 0.74 mmol) in 20 ml of N,N-dimethylformamide in an atmosphere of N2. After 5 min, 2,4-Dichloro-benzoyl chloride (310 mg, 1.48 mmol) was added to the solution and then the reaction mixture was stirred for 30 min at 0° C. and 16 h at room temperature. The mixture was partitioned between ether (20 mL) and water (20 mL) and the organic layer was separated. The aqueous phase was washed twice with ether (2×10 mL) and the combined ether layer was dried (MgSO4), concentrated and the residue was purified by preparative chromatography (30% EtOAc/Hexane) to obtain 58 mg (16%) of 3-[(2,4-Dichloro-benzoyl)-phenyl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): 7.65-7.10 ppm (m, 14H, Haro); 3.77 ppm (s, 3H).

Workup

  1. customThe mixture was partitioned between ether (20 mL) and water (20 mL)
  2. customthe organic layer was separated
  3. washThe aqueous phase was washed twice with ether (2×10 mL)
  4. dry with materialthe combined ether layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified by preparative chromatography (30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-4b288f5edbdd445abb5502c767478c5c
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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