Sodium Hydroxide → HCID 21891837, compound

HRID 720682Notes

Reaction equation

HRID 720682 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10](=[O:12])[NH2:11])=[O:4].[OH-].[Na+]>CO>[C:10]([C:9]1[CH:8]=[CH:7][S:6][C:5]=1[C:3]([OH:4])=[O:2])(=[O:12])[NH2:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2807577HCID 2807577, compound

Product 1

HCID 21891837HCID 21891837, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-carbamoyl-thiophene-2-carboxylic acid methyl ester (125 mg, 0.67 mmol) in methanol (2.0 mL) at 25° C. was treated with a 1N aqueous sodium hydroxide solution (2.0 mL, 2.02 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (10 mL) and then acidified to pH=2 with a 1N aqueous hydrochloric acid solution. The resulting slurry was cooled to 0° C. The solids were collected by filtration, washed with water, and dried in vacuo to afford 3-carbamoyl-thiophene-2-carboxylic acid (102 mg, 88.3%) as an off-white solid: LR-MS for C6H5NO3S (M−H)+ at m/z=170.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. additionThe residue was diluted with water (10 mL)
  3. temperatureThe resulting slurry was cooled to 0° C
  4. filtrationThe solids were collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b3312e7cc6734b48a1e50f2fd3ad38a2
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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