Sodium Hydroxide → HCID 59468598, compound

HRID 1012173Notes

Reaction equation

HRID 1012173 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=1)=O.[C:16]1([CH3:26])[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([NH2:25])=[NH:24])[CH:17]=1.[OH-].[Na+]>COCCO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:16]1([CH3:26])[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]2[N:25]=[C:5]([C:7]3[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=3)[CH:4]=[CH:3][N:24]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67313456HCID 67313456, compoundHCID 178425553HCID 178425553, compound

Product 1

HCID 59468598HCID 59468598, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

5-(3-dimethylamino-acryloyl)thiophene-2-carboxylic acid (200 mg, 0.888 mmol), N-m-tolylguanidine (71.1 mg, 1.77 mmol) and NaOH (264 mg, 1.77 mmol) were dissolved in 2-methoxyethanol (2 mL) and heated at 100° C. for 48 hours. After cooling, the reaction was diluted with 10% Aqueous citric acid solution and the solids were collected by filtration. The solids were washed with water and Et2O and dried to afford 5-(2-m-tolylamino-pyrimidin-4-yl)thiophene-2-carboxylic acid (149 mg, 53.8%) as a yellow solid. MS: m/z 312 (M+H+).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solids were collected by filtration
  3. washThe solids were washed with water and Et2O
  4. customdried

Sources & evidence

ORD record
ord-894fdff2a15d4e17878eb8adf3dd0f1c
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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