Ammonium Hydroxide → HCID 44224964, compound

HRID 1666192Notes

Reaction equation

HRID 1666192 reaction equation
CS(O[CH2:6][C:7]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:9]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:8]=1)(=O)=O.[NH4+:27].[OH-]>C1COCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]2[N:9]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[N:8]=[C:7]([CH2:6][NH2:27])[CH2:11]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 59411008HCID 59411008, compound

Product 1

HCID 44224964HCID 44224964, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-yl]methyl methanesulfonate (58 g, 0.134 mol) in THF (200 mL) and NH4OH aq. (25%, 412 mL, 2.68 mol) was stirred at room temperature for 15 hours. The excess ammonia was removed in vacuo and EtOAc (200 mL) and sat. aq. NaHCO3 (150 mL) was added. The organic layer was separated and the aqueous phase was extracted with EtOAc, the combined organic layers were washed with sat. aq. NaHCO3 (2×150 mL), brine (200 mL) and water (1×200 mL), dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to afford the crude material (89.85 g). This material was purified by column chromatography using dichloromethane, methanol and ammonium hydroxide (97:3:1) in silica gel to yield the [5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-yl]methyl amine (18.90 g, 40%, two steps) as a yellow solid.

Workup

  1. customThe excess ammonia was removed in vacuo and EtOAc (200 mL) and sat. aq. NaHCO3 (150 mL)
  2. additionwas added
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washthe combined organic layers were washed with sat. aq. NaHCO3 (2×150 mL), brine (200 mL) and water (1×200 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customto afford the crude material (89.85 g)
  9. customThis material was purified by column chromatography

Sources & evidence

ORD record
ord-ddeffef164a14538a873a3af623a6a7f
Source dataset
uspto-grants-2011_10
Patent number
US08044053B2

Reaction notes

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