Sodium Hydroxide → HCID 18005458, compound

HRID 2301382Notes

Reaction equation

HRID 2301382 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([CH3:23])=[O:22].Br[CH2:25][C:26]([NH2:28])=[O:27].[OH-].[Na+]>C(#N)C.O.C(=O)([O-])[O-].[Ca+2]>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([NH:1][CH2:25][C:26]([NH2:28])=[O:27])=[C:3]([S:21]([CH3:23])=[O:22])[C:4]([C:19]#[N:20])=[N:5]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 696322-BromoacetamideHCID 10861895HCID 10861895, compound

Product 1

HCID 18005458HCID 18005458, compoundYield 15.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 10112Calcium CarbonateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carbonitrile (0.5 g) in acetonitrile was added 2-bromoacetamide (0.18 g) in water and calcium carbonate (0.13 g). The mixture was heated under reflux for 1.5 hours, cooled to 25° C. and a solution of sodium hydroxide (0.05 g) in water added. This was then heated under reflux for one hour, evaporated and the residue purified by preparative thin-layer chromatography eluting first with 20% methanol in dichloromethane to give 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-5-[(aminocarbonylmethyl)amino]-1H-pyrazole-3-carbonitrile (0.089 g), m.p.155-157° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureThis was then heated
  4. temperatureunder reflux for one hour
  5. customevaporated
  6. customthe residue purified by preparative thin-layer chromatography
  7. washeluting first with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-1b782d6fe7e646b1b869b8898cfbc67a
Source dataset
uspto-grants-2002_12
Patent number
US06500850B2

Reaction notes

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