Triethylamine → HCID 21082665, compound

HRID 2278408Notes

Reaction equation

HRID 2278408 reaction equation
Cl.[CH3:2][O:3]CN.C([N:8]([CH2:11]C)CC)C.[CH3:13][C:14]1[O:15][CH:16]=[CH:17][C:18]=1[C:19](Cl)=[O:20]>ClCCl.O>[CH3:11][N:8]([O:3][CH3:2])[C:19]([C:18]1[CH:17]=[CH:16][O:15][C:14]=1[CH3:13])=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27598502-Methylfuran-3-carbonyl chlorideHCID 21959107Methoxymethanamine hydrochloride

Product 1

HCID 21082665HCID 21082665, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of methoxymethylamine hydrochloride (5.85 g, 60.0 mmol) and triethylamine (16.73 ml, 120 mmol) in dichloromethane (100 ml) was stirred at 0° C. A solution of 2-methyl-3-furancarbonyl chloride (7.23 g, 50 mmol) in dichloromethane (20 ml) was added and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with water. The organic layer was separated, washed with saturated sodium hydrogen carbonate solution, water and brine, dried and evaporated to give the title compound as an oil (6.7 g, 79%); LC/MS [M+H]+=170.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with saturated sodium hydrogen carbonate solution, water and brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-742d573aebaf43fc9fb15d2a1c84a21d
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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