Dichloromethane → HCID 18980925, compound

HRID 482616Notes

Reaction equation

HRID 482616 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([NH:17][CH3:18])[C:14]([C:19]3[CH:24]=[CH:23]C(Cl)=[CH:21][CH:20]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].[N:30]#[C:31]Br.[CH2:33]([Cl:35])Cl>>[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([N:17]([CH3:18])[C:31]#[N:30])[C:14]([C:19]3[CH:24]=[CH:23][C:33]([Cl:35])=[CH:21][CH:20]=3)=[N:13]2)=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 18981009HCID 18981009, compound

Product 1

HCID 18980925HCID 18980925, compound

Procedure

To 4.0 g (10 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-(N-methylamino)-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 116) in 100 ml of methylene chloride was added 10 ml of 1.0M aqueous NaOH and 1.2 g (11.3 mmole) of cyanogen bromide dissolved in 5 ml of methylene chloride. After stirring overnight, the organic layer was separated, concentrated in vacuo, and triturated with diethyl ether to yield the title compound, a white solid, mp 216°-217° C.

Workup

  1. customthe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-37a7c687f1a94c21823cbf8bf462be7c
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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