Water → 2-(2-Ethoxycarbonyl-acetylamino)-4-phenyl-thiophene-3-carboxylic acid ethyl ester

HRID 215982Notes

Reaction equation

HRID 215982 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:17])=[O:5])[CH3:2].C(N([CH2:23][CH3:24])CC)C.C([CH:27]([C:31](Cl)=[O:32])[C:28](Cl)=[O:29])C.[OH2:34]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH:17][C:31](=[O:32])[CH2:27][C:28]([O:29][CH2:23][CH3:24])=[O:34])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylateHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 684322622-(2-Ethoxycarbonyl-acetylamino)-4-phenyl-thiophene-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-4-phenyl-thiophene-3-carboxylic acid ethyl ester (5.0 g, 0.02M) was dissolved in anhydrous dichloromethane (150 ml). Triethylamine (5.56 ml, 0.04M) was added and the mixture cooled to 0° C. Ethyl Malonyl Chloride (3.79 ml, 0.03M) was added over 5 min maintaining the temperature at 0° C. The reaction was then stirred at room temperature for 1 hr. Water (100 ml) was added and the organic layer separated. The aqueous layer was extracted with a further 100 ml of dichloromethane. The organics were combined, washed with water (2×100 ml) and dried over sodium sulphate. The concentrated residues were columned on silica, eluting with ethylacetate-cyclohexane 5-10% v/v. Pure fractions were combined and concentrated and the residues triturated with hexane, decanted and dried to give 2-(2-ethoxycarbonyl-acetylamino)-4-phenyl-thiophene-3-carboxylic acid ethyl ester as a white solid. Yield=6.95 g (96.2%).

Workup

  1. temperaturemaintaining the temperature at 0° C
  2. customthe organic layer separated
  3. extractionThe aqueous layer was extracted with a further 100 ml of dichloromethane
  4. washwashed with water (2×100 ml)
  5. dry with materialdried over sodium sulphate
  6. washeluting with ethylacetate-cyclohexane 5-10% v/v
  7. concentrationconcentrated
  8. customthe residues triturated with hexane
  9. customdecanted
  10. customdried

Sources & evidence

ORD record
ord-fb1500d37d6548b4bfe6d19f6fd84e5b
Source dataset
uspto-grants-2012_06
Patent number
US08193215B2

Reaction notes

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