Thionyl Chloride → 3,5-Diamino-2-methylbenzoic acid
Reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[NH2:15])[C:9]([OH:11])=[O:10].[C:16](=O)(O)[O-].[Na+]>CO>[CH3:16][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([NH2:15])=[C:6]([NH2:5])[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To dry methanol (20 ml) was carefully added thionyl chloride (1 ml) dropwise with stirring. The 3,4-diaminobenzoic acid (1 g) was added in portions at R.T. with stirring then the mixture heated at reflux for 3 h. Saturated sodium bicarbonate was added until the mixture was basic, then the mixture extracted into chloroform containing 25% methanol. The extract was dried and evaporated in vacuo to give the product (0.88 g, 81%) as a brown crystalline solid.
Workup
- stirringwith stirring
- temperaturethe mixture heated
- temperatureat reflux for 3 h
- extractionthe mixture extracted into chloroform containing 25% methanol
- customThe extract was dried
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-79f45971a6444b508008851ae0cf9325
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745490B2
Reaction notes
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