Triethylamine → HCID 20775751, compound

HRID 2193913Notes

Reaction equation

HRID 2193913 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].C(N(CC)CC)C.[Cl:24][C:25]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:32]([Cl:34])=[CH:33][C:25]=1[Cl:24])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

Product 1

HCID 20775751HCID 20775751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a ice-cold solution of 3-Amino-5-phenyl-thiophene-2-carboxylic acid methyl ester 1 (5 g, 21.5 mmol) and triethylamine (4.56 g, 45.0 mmol) in dichloromethane (100 ml) was added 2,4-dichlorobenzoyl chloride (3.90 g, 19.4 mmol). The reaction mixture was stirred for 30 min a 0° C. and 16 h at room temperature. Then, the reaction mixture was partitioned between 25 ml of H2O, 50 ml sat. NaHCO3 and 50 ml of CH2Cl2. The organic layer was separated and the aqueous phase was washed twice with CH2Cl2 (2×50 mL). The combined dichloromethane layer was dried (MgSO4), concentrated and the residue was purified by recrystallization in CH2Cl2 to obtain 5.832 g (74%) as a white solid of 3-(2,4-Dichloro-benzoylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): 8.30 ppm (s, 1H, Haro); 7.74-7.66 ppm (m, 3H, Haro); 7.51 ppm (d, 1H, Haro); 7.46-7.34 ppm (m, 4H, Haro); 3.91 ppm (s, 3H).

Workup

  1. customThen, the reaction mixture was partitioned between 25 ml of H2O, 50 ml sat. NaHCO3 and 50 ml of CH2Cl2
  2. customThe organic layer was separated
  3. washthe aqueous phase was washed twice with CH2Cl2 (2×50 mL)
  4. dry with materialThe combined dichloromethane layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified by recrystallization in CH2Cl2

Sources & evidence

ORD record
ord-dec0bd069922418a8d29b0cd7195f9a7
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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