Hydrochloric Acid → 4-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid

HRID 583768Notes

Reaction equation

HRID 583768 reaction equation
[OH-].[K+].C[O:4][C:5]([C:7]1[S:8][C:9]([CH3:23])=[C:10]([NH:12][C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH:11]=1)=[O:6].Cl>CO.O>[CH3:23][C:9]1[S:8][C:7]([C:5]([OH:6])=[O:4])=[CH:11][C:10]=1[NH:12][C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 101931415-Methyl-4-(3-benzyl-ureido)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 223425214-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 2N aqueous potassium hydroxide solution (16 mL) was added to a stirred solution of 5-methyl-4-(3-benzyl-ureido)-thiophene-2-carboxylic acid methyl ester from Step 2 of Example 16 below (0.4 g, 1.3 mmol) in warm methanol (4 mL), and the mixture was heated under reflux. After 1 hour the mixture was cooled, 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 0.29 g of 5-methyl-4-(3-benzyl-ureido)-thiophene-2-carboxylic acid; mp 259-260° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureAfter 1 hour the mixture was cooled
  4. filtrationThe precipitate was filtered off
  5. washrinsed with water
  6. dry with materialethanol, then ether, and dried

Sources & evidence

ORD record
ord-1bd0e146d099435aba18930236eb8688
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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