Triphenylphosphine → 3-[Isopropyl-(4-oxo-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 73163Notes

Reaction equation

HRID 73163 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:9]=1[NH:10][CH:11]([CH3:13])[CH3:12])=[O:4].ClNC(=O)CCC(N)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:48]=[C:49]1[CH2:54][CH2:53][CH:52]([C:55](O)=[O:56])[CH2:51][CH2:50]1>ClCCCl.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:8][C:9]=1[N:10]([CH:11]([CH3:13])[CH3:12])[C:55]([CH:52]1[CH2:53][CH2:54][C:49](=[O:48])[CH2:50][CH2:51]1)=[O:56])=[O:4]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 1927304-Oxocyclohexanecarboxylic acidHCID 11737447Methyl 3-(isopropyl-amino)-5-phenylthiophene-2-carboxylateHCID 15238416N-chlorosuccinamide

Product 1

HCID 597523673-[Isopropyl-(4-oxo-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-Isopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester (1.5 g, 5.45 mmol) in 1,2-dichloroethane, N-chlorosuccinamide (0.940 g, 7.091 mmol), triphenylphosphine (1.9 g, 7.091 mmol) and 4-oxo-cyclohexanecarboxylic acid (800 mg, 5.455 mmol) were added. The reaction mixture was stirred at reflux for overnight under an atmosphere of N2. The reaction mixture was diluted with CH2Cl2 and extracted with saturated solution oh NaHCO3. The organic layer was separated, dried (Na2SO4) and concentrated. The residue was purified using silica gel column chromatography using ethyl acetate:hexane (1:4) as eluent to obtain 3-[Isopropyl-(4-oxo-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester. (1.2 g, 55%) as syrup. 1H NMR (CDCl3, 400 MHz): δ7.75-7.50 (m, 2H), 7.70-7.38 (m, 3H), 7.12 (s, 1H), 4.95 (m, 1H), 3.87 (s, 3H), 2.75-0.83 (m, 15H).

Workup

  1. temperatureat reflux for overnight under an atmosphere of N2
  2. extractionextracted with saturated solution oh NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-f136c2155e5048dbbc5cd26ffa9647f9
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Reaction notes

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