HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → HCID 18005458, compound

HRID 1700406
Notes
Print preview

Reaction equation

HRID 1700406 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 696322-BromoacetamideHCID 108618955-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-methylsulfinylpyrazole

Product 1

HCID 18005458HCID 18005458, compoundYield 15.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×
HCID 6342
Acetonitrile
Solvent
HCID 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-72d7810042d246c08573f30004d4f6e9
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06350771B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes