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Water → 4-(2-{1-[5-(2,3-Dihydro-1H-inden-5-yl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazinecarbothioamido)benzoic acid

HRID 337385
Notes
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Reaction equation

HRID 337385 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]([CH3:15])[N:13]=[C:12]([C:16](=[N:18][NH2:19])[CH3:17])[C:11]=3[OH:20])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)=[C:22]=[S:23].O>CN(C)C=O>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]([CH3:15])[N:13]=[C:12]([C:16](=[N:18][NH:19][C:22](=[S:23])[NH:21][C:24]4[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:31][CH:32]=4)[CH3:17])[C:11]=3[OH:20])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 2429464-Isothiocyanatobenzoic acidHCID 866694035-(2,3-Dihydro-1H-inden-5-yl)-3-(1-hydrazonoethyl)-1-methyl-1H-pyrazol-4-ol

Product 1

HCID 866694024-(2-{1-[5-(2,3-Dihydro-1H-inden-5-yl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazinecarbothioamido)benzoic acidYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

5-(2,3-Dihydro-1H-inden-5-yl)-3-(1-hydrazonoethyl)-1-methyl-1H-pyrazol-4-ol (47 mg, 0.174 mmol) in N,N-dimethylformamide (0.94 mL) was stirred with 4-isothiocyanatobenzoic acid (33 mg, 0.184 mmol) at room temperature for 4 hours and 40 minutes. After the reaction, 0.94 mL of water was added, and the resulting pale yellow solid was collected by filtration, washed with water and dried under reduced pressure to obtain the desired product (62 mg, 79% yield).

Workup

  1. additionwas added
  2. filtrationthe resulting pale yellow solid was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-e35be99e862b48b4aa1753610dc4226d
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889732B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes