Hydrochloric Acid → 5-Methyl-4-phenylacetylamino-thiophene-2-carboxylic acid benzyl ester

HRID 583762Notes

Reaction equation

HRID 583762 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([O:18][C:19]([C:21]1[S:22][C:23]([CH3:27])=[C:24]([NH2:26])[CH:25]=1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.Cl>O1CCCC1.O>[CH2:11]([O:18][C:19]([C:21]1[S:22][C:23]([CH3:27])=[C:24]([NH:26][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:25]=1)=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 613104205-Methyl-4-amino-thiophene-2-carboxylic acid benzyl ester

Product 1

HCID 101938015-Methyl-4-phenylacetylamino-thiophene-2-carboxylic acid benzyl esterYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phenylacetyl chloride (0.26 g, 1.7 mmol) was added to a stirred solution of 5-methyl-4-amino-thiophene-2-carboxylic acid benzyl ester (0.4 g, 1.6 mmol), prepared as described above in Step 2, and diisopropylethylamine (0.26 g, 2.0 mmol) in tetrahydrofuran (15 mL) under an inert atmosphere at room temperature. After 18 hours, the mixture was diluted with water (100 mL) and acidified with aqueous HCl. The precipitate was filtered off, rinsed with water, then ethanol, then ether, and dried to afford 0.3 g of 5-methyl-4-phenylacetylamino-thiophene-2-carboxylic acid benzyl ester. Recrystallization of a sample from acetonitrile gave product with a mp 173-174° C.

Workup

  1. customprepared
  2. filtrationThe precipitate was filtered off
  3. washrinsed with water
  4. dry with materialethanol, then ether, and dried

Sources & evidence

ORD record
ord-e02c4ca35b204798b7b6d09718cae3b8
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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