4-Hydrazinobenzoic acid → HCID 53641587, compound
Reaction equation
[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].[NH:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[NH2:18]>>[NH2:2][C:1]1[N:17]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=2)[N:18]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]Participants
3
Procedure
The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl)-acrylamide (464 mg, 2.0 mmol) and 4-hydrazinobenzoic acid (334 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was purified by column chromatography (SiO2, 5-10% methanol +2% acetic acid in CH2Cl2) and by trituration with methanol to give the title compound as a light yellow solid (497 mg) m.p. >310° dec. δH (d6DMSO) 8.06 (2H, d, J 8.7 Hz), 7.75 (2H, d, J 8.6 Hz), 7.48 (2H, d, J 8.1 Hz), 7.29 (2H, d, J 8.0 Hz), 6.63 (2H, br s) and 2.36 (3H, s), carboxyl proton and amino protons not observed.
Workup
- customThe crude product was purified by column chromatography (SiO2, 5-10% methanol +2% acetic acid in CH2Cl2) and by trituration with methanol
Sources & evidence
- ORD record
- ord-86b8baa550b7466dbd2e45ba602726d4
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05922741
Reaction notes
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