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Triethylamine → HCID 14835675, compound

HRID 1709242
Notes
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Reaction equation

HRID 1709242 reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](O)=[O:8].C(N(CC)CC)C.C(Cl)(=O)OCC.O.[NH2:29][NH2:30]>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:29][NH2:30])=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24654Hydrazine hydrate (1:1)HCID 148356743-(Dimethoxymethyl)benzoic acid

Product 1

HCID 14835675HCID 14835675, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
-55 °C

Procedure

3.92 g of 3-dimethoxymethylbenzoic acid and 2.22 g of triethylamine were dissolved in 40 ml of methylene chloride. To the solution was dropwise added 2.28 g of ethyl chlorocarbonate at -30° to -20° C. The mixture was stirred for 30 minutes at the same temperature. The mixture was then cooled to -55° C., and 5.00 g of hydrazine hydrate was added thereto. The temperature of the mixture was elevated to room temperature. The methylene chloride layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: chloroform/ethanol=30/1) to obtain 4.13 g of colorless oily 3-dimethoxymethylbenzhydrazide.

Workup

  1. customat -30° to -20° C
  2. customwas elevated to room temperature
  3. customThe methylene chloride layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by a column chromatography (eluant: chloroform/ethanol=30/1)

Sources & evidence

ORD record
ord-18ef36b78ea44a8d85845e99928a62e3
Source dataset
uspto-grants-1990_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04948796

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes