Trichloroacetyl chloride → HCID 91021533, compound

HRID 1178455Notes

Reaction equation

HRID 1178455 reaction equation
[NH2:1][C:2]([C:4]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[CH:11][CH:12]=1)=O.C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O>ClCCl>[Cl:26][C:23]1[CH:24]=[CH:25][C:4]([C:2]#[N:1])=[C:5]([CH:22]=1)[O:6][C:7]1[CH:8]=[C:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chloride2×HCID 8471TriethylamineHCID 91496015HCID 91496015, compound

Product 1

HCID 91021533HCID 91021533, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

The above amide (490 mg) and triethylamine (0.37 ml) in dichloromethane (10 ml) was treated dropwise with trichloroacetyl chloride (0.16 ml) in dichloromethane (10 ml) with stirring at 0-5° C. After 0.5 h, more trichloroacetyl chloride (0.8 ml) was added and stirring continued for 0.25 h. The reaction mixture was washed with aqueous sodium bicarbonate solution, dilute hydrochloric acid, water, then brine, and dried (MgSO4). The solvent was evaporated and the residue was purified by chromatography (silica gel, dichloromethane as eluent) to give 1,1-dimethylethyl {[3-(5-chloro-2-cyanophenoxy)phenyl]methyl}carbamate (240 mg) as a colourless solid.

Workup

  1. stirringstirring
  2. waitcontinued for 0.25 h
  3. washThe reaction mixture was washed with aqueous sodium bicarbonate solution, dilute hydrochloric acid, water
  4. dry with materialbrine, and dried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue was purified by chromatography (silica gel, dichloromethane as eluent)

Sources & evidence

ORD record
ord-32031b4d3d9f41f3b4615b7d1fa146ff
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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