Hydrochloric Acid → HCID 69693616, compound

HRID 583763Notes

Reaction equation

HRID 583763 reaction equation
C(N(C(C)C)CC)(C)C.Cl.[CH3:11][C:12]1[S:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][C:13]=1[NH2:20].[C:21]1([CH2:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>O1CCCC1.O>[CH3:11][C:12]1[S:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][C:13]=1[NH:20][C:28](=[O:29])[CH2:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 696934604-Amino-5-methylthiophene-2-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 69693616HCID 69693616, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (3.33 g, 25.8 mmol) was added to a stirred suspension of 5-methyl-4-amino-thiophene-2-carboxylic acid hydrochloride (1.4 g, 7.0 mmol) in tetrahydrofuran (25 mL) under an inert atmosphere at room temperature. After 1½ hours, phenylacetyl chloride (1.1 g, 7.2 mmol) was added. After 24 hours, the mixture was diluted with water (200 mL) and acidified with dilute aqueous hydrochloric acid. After 12 hours the precipitate was filtered off, rinsed with water, and dried to afford 1.5 g of 5-methyl-4-phenylacetylamino-thiophene-2-carboxylic acid. Recrystallization of a sample from acetonitrile gave product with a mp 249-250° C.

Workup

  1. waitAfter 1½ hours
  2. filtrationAfter 12 hours the precipitate was filtered off
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-b5f80b1799c9408cbb78765dbb03a0ab
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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