Water → HCID 68294330, compound

HRID 2279482Notes

Reaction equation

HRID 2279482 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH2:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:15](Cl)(=[O:26])[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.N1C=CC=CC=1.O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:14][C:15](=[O:26])[O:16][C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[C:10]([F:11])([F:12])[F:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 433445253,4-Dichloro-α-(trifluoromethyl)benzenemethanamine

Product 1

HCID 68294330HCID 68294330, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 148 (1.00 g, 4.01 mmol), 4-nitrophenyl carbonochloridate (0.9085 g, 4.507 mmol) and pyridine (0.7131 g, 9.015 mmol) in DCM (10 mL) were stirred for 30 min. Water was added and the reaction mixture was extracted with DCM. The organic layer was concentrated and purified by SiO2 chromatography eluting with 20% EtOAc/hexane to afford 1.511 g (90.0%) of 4-nitrophenyl 1-(3,4-dichlorophenyl)-2,2,2-trifluoroethylcarbamate (150).

Workup

  1. extractionthe reaction mixture was extracted with DCM
  2. concentrationThe organic layer was concentrated
  3. custompurified by SiO2 chromatography
  4. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-6a73b7652f5444e690bb4d495dfcc7ea
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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