Triethylamine → N-{[5-Amino-4-(2-chlorobenzoyl)thiophen-2-yl]carbonyl}glycine ethyl ester

HRID 1197121Notes

Reaction equation

HRID 1197121 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][C:3]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17].S(Cl)(Cl)=O.Cl.[CH2:24]([O:26][C:27](=[O:30])[CH2:28][NH2:29])[CH3:25].C(N(CC)CC)C>ClCCl>[CH2:24]([O:26][C:27](=[O:30])[CH2:28][NH:29][C:7]([C:5]1[S:6][C:2]([NH2:1])=[C:3]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH:4]=1)=[O:9])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 13670763HCID 13670763, compound

Product 1

HCID 13961234N-{[5-Amino-4-(2-chlorobenzoyl)thiophen-2-yl]carbonyl}glycine ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

14.0 g (50 mmol) of 5-amino-4-(2-chlorobenzoyl)-thiophene-2-carboxylic acid [the synthesis is carried out analogously to Hromatka et al., Monatsh. Chem. 104, 973 (1973)] are suspended in 250 ml of anhydrous dichloromethane, 8 ml of thionyl chloride are added dropwise, and the mixture is stirred at room temperature for 2.5 hours. It is then evaporated in vacuo, the residue is taken up in dichloromethane, and the solution is added dropwise to a mixture of 7 g (50 mmol) of glycine ethyl ester hydrochloride and 16 ml of triethylamine in 100 ml of anhydrous dichloromethane. After 1 our at room temperature the mixture is extracted with water. The residue from the concentrated organic phase is worked up by chromatography on silica gel. 8.1 g (44% of theory) of the title compound of melting point 216°-218° C. are obtained.

Workup

  1. customIt is then evaporated in vacuo
  2. extractionAfter 1 our at room temperature the mixture is extracted with water

Sources & evidence

ORD record
ord-317a5d3188c24bf28ad8affc508d1408
Source dataset
uspto-grants-1992_05
Patent number
US05116971

Reaction notes

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