Chloroacetyl chloride → HCID 68674620, compound

HRID 2358462Notes

Reaction equation

HRID 2358462 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[Cl:17])[C:10]([C:18]([NH:20][NH2:21])=[O:19])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:28][CH2:29][C:30](Cl)=[O:31].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:28][CH2:29][C:30]([N:20]([C:18]([C:10]1[C:11]2[C:16](=[C:15]([Cl:17])[CH:14]=[CH:13][CH:12]=2)[N:8]([CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:9]=1)=[O:19])[NH2:21])=[O:31]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 68675033HCID 68675033, compound

Product 1

HCID 68674620HCID 68674620, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-cyclohexylmethyl-7-chloro-1H-indole-3-carboxylic acid hydrazide (0.71 g, 2.3 mmol) in dichloromethane (20 ml) was added potassium carbonate (1.6 g, 11 mmol) and the reaction stirred for 1 h. The reaction mixture was cooled in a dry ice/ethanol bath and chloroacetyl chloride (0.2 ml, 3.0 mmol) was added and the reaction stirred for 1 h. Saturated sodium bicarbonate solution (30 ml) was added and the reaction allowed to warm to room temperature. The reaction mixture was extracted with 9:1 (v/v) dichloromethane:methanol (3×20 ml), the organic phases combined, washed with brine (1×30 ml), dried over sodium sulfate, and solvent removed in vacuo to give 1-cyclohexylmethyl-7-chloro-1H-indole-3-carboxylic acid N-(2-chloroacetyl)hydrazide (0.6 g, 2.0 mmol).

Workup

  1. temperatureThe reaction mixture was cooled in a dry ice/ethanol bath
  2. stirringthe reaction stirred for 1 h
  3. extractionThe reaction mixture was extracted with 9:1 (v/v) dichloromethane
  4. washwashed with brine (1×30 ml)
  5. dry with materialdried over sodium sulfate, and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-8ff9a5e29b6e4ac0ad2f83e23cb6ec5a
Source dataset
uspto-grants-2010_07
Patent number
US07763732B2

Reaction notes

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