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

Dichloromethane → Flucofuron

HRID 2110087
Notes
Print preview

Reaction equation

HRID 2110087 reaction equation
N[C:2]1O[N:5]=[C:4]([C:7]([CH3:10])(C)C)[CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][C:13]=1[C:21]([F:24])([F:23])[F:22].[CH2:25]([Cl:27])Cl>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:20])[NH:5][C:4]2[CH:7]=[CH:10][C:25]([Cl:27])=[C:2]([C:21]([F:24])([F:23])[F:22])[CH:3]=2)=[CH:14][C:13]=1[C:21]([F:22])([F:23])[F:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzene

Product 1

HCID 67788Flucofuron

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 5-amino-3-tert-butylisoxazole (0.100 g) in anh toluene (5 mL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.395 g). The reaction vessel was sealed, heated at 85° C. for 24 h, and cooled to room temp. The reaction mixture was added to a slurry of Dowex® 50WX2-100 resin (0.5 g) in CH2Cl2 (40 mL), and the resulting mixture was stirred vigorously for 72 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (gradient form 100% CH2Cl2 to 5% MeOH/95% CH2Cl2) to give bis(4-chloro-3-(trifluoromethyl)phenyl)urea followed by N-(3-tert-butyl-5-isoxazolyl)-N′-(4-chloro-3-(trifluoromethyl)phenyl)urea. The residue from the symmetrical urea fractions was triturated (Et2O/hexane) to give the urea as a white solid (0.110 g): TLC (3% MeOH/97% CH2Cl2) Rf 0.55; FAB-MS m/z 417 ((M+H)+). C. Urea Interconversions and Misc. Reactions C1. General Method for Alkylation of Hydroxyphenyl Ureas

Workup

  1. customThe reaction vessel was sealed
  2. temperaturecooled to room temp
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (gradient form 100% CH2Cl2 to 5% MeOH/95% CH2Cl2)

Sources & evidence

ORD record
ord-3acf076f77fc46edb836d65e9c692f71
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07517880B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes