Water → HCID 67303134, compound

HRID 888764Notes

Reaction equation

HRID 888764 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][NH:12][C:13]([O-:15])=[O:14])[CH2:8]2.C(=O)([O-])O.[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24].O>ClCCl>[Cl:21][CH2:22][C:23]([N:11]([CH:2]1[CH:3]2[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:1]1[CH2:10]3)[CH2:9]2)[NH:12][C:13]([O:15][CH2:10][C:1]1[CH:8]=[CH:7][CH:9]=[CH:3][CH:2]=1)=[O:14])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 131729910HCID 131729910, compound

Product 1

HCID 67303134HCID 67303134, compoundYield 144.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, a solution of 2-(adamantan-2-yl)hydrazinecarboxylate (800 mg, 2.66 mmol) in dichloromethane (30 mL) was added with sodium hydrogen carbonate (450 mg, 5.40 mmol) and chloroacetic acid chloride (300 mg, 2.66 mmol) were added at 0° C., and the resultant was stirred at room temperature for 3 hours. The reaction solution was added with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and benzyl 2-(2-chloroacetyl)-2-(adamantan-2-yl)hydrazinecarboxylate (726 mg, 72.4%) was obtained as a white crystalline powder.

Workup

  1. additionwere added at 0° C.
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f49c019b99846cc80978ae6ee17f89b
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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