Nitrogen → 3-[tert-Butyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 1015636Notes

Reaction equation

HRID 1015636 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:9]=1[NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:4].N#N.[Cl:23][C:24]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>ClC(Cl)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:9]=1[N:10]([C:11]([CH3:14])([CH3:12])[CH3:13])[C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:24]=1[Cl:23])=[O:4]

Participants

5

Reactant 3

HCID 947NitrogenHCID 666452,4-Dichlorobenzoyl chlorideHCID 207757713-tert-Butylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 207757533-[tert-Butyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl esterYield 69.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-tert-Butylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester (100 mg, 0.35 mmol) in dichloroethane (10 ml) in an atmosphere of N2 was added 2,4-dichloro-benzoyl chloride (79 mg, 0.38 mmol). The reaction mixture was stirred for 16 h at reflux. Then, the solvents were removed and the residue was purified by flash chromatography (9:1 Hexane/EtOAc) to obtain 112 mg (69%) of 3-[tert-Butyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): 7.50 ppm (m, 2H, Haro) 7.44-7.34 ppm (m, 3H, Haro); 7.27 ppm (s, 1H, Haro); 7.18 ppm (dl, 1H, Haro); 7.14 ppm (d, 1H, Haro); 7.00 ppm (dd, 1H, Haro); 3.93 ppm (s, 3H); 1.56 ppm (s, 9H).

Workup

  1. temperatureat reflux
  2. customThen, the solvents were removed
  3. customthe residue was purified by flash chromatography (9:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-11774a8273c64678b6bfcff235a19199
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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