Sodium Hydroxide → HCID 178514156, compound

HRID 1452763Notes

Reaction equation

HRID 1452763 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Br:13])[CH:3]=1.C([N:22]=[C:23]=[S:24])(=O)C1C=CC=CC=1.[OH-].[Na+].[NH4+].[Cl-]>C1COCC1>[Br:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:3]=[C:2]([NH:1][C:23]([NH2:22])=[S:24])[NH:6][N:5]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 68284Benzoyl isothiocyanateHCID 178507275HCID 178507275, compound

Product 1

HCID 178514156HCID 178514156, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-3-(2-bromophenyl)pyrazole (1.3 g, 5.46 mmol) in THF (20 mL) was added dropwise benzoyl isothiocyanate (0.81 mL, 6.0 mmol). The reaction mixture was stirred at room temperature for 3 hours, then 4 N aqueous solution of NaOH (4 mL) was added, and the reaction mixture was further stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, neutralized to pH 7 with a saturated solution of NH4Cl, and extracted with EtOAc (3×). The combined organic layers were directly purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent to provide 1.62 g (quant.) of [5-(2-bromo-phenyl)-2H-pyrazol-3-yl]-thiourea as a yellowish foam. 1H-NMR (d6-DMSO) δ: 12.8 (broad s, 1H), 10.4 (broad s, 1H), 8.99 (broad s, 1H), 8.52 (broad s, 1H), 7.76 (d, 1H), 7.50 (m, 2H), 7.36 (t, 1H), 6.24 (broad s, 1H).

Workup

  1. stirringthe reaction mixture was further stirred at 50° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with EtOAc (3×)
  4. customThe combined organic layers were directly purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-766125ce784d43dcbf47dc9fe27f6b3c
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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