Triethylamine → HCID 20775751, compound

HRID 1015629Notes

Reaction equation

HRID 1015629 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-702c15132da64e7aa89068acee6810dd
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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