Water → HCID 67272012, compound

HRID 1696500Notes

Reaction equation

HRID 1696500 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[OH-].[Na+].[C:12](Cl)([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13].O>CCOC(C)=O>[Cl:17][C:16]([Cl:19])([Cl:18])[CH2:15][O:14][C:12](=[O:13])[NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 118442,3-DichloroanilineHCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 67272012HCID 67272012, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,3-dichloroaniline (0.200 g, 1.23 mmol) in EtOAc (5 mL) was added NaOH (1M, 2 mL, 2 mmol) and Troc-Cl (0.262 g, 1.23 mmol) and the resulting mixture was stirred overnight. Water (50 mL) was added and the mixture was extracted with EtOAc (3×100 mL), dried (MgSO4), concentrated and purified via column chromatography to yield 2,2,2-trichloroethyl-2,3-dichlorophenylcarbamate (408 mg, 98%) as a yellow foam. 1H NMR (400 MHz, CDCl3): δ 8.11 (d, J=6.4 Hz, 1H), 7.43 (brs, 1H), 7.25-7.22 (m, 2H), 4.86 (s, 2H); MS (EI) m/z: 335.8 (M+H+).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-cc3bad52dc51420fae36c5cc7a354884
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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