Ethylamine → HCID 21691262, compound

HRID 1911727Notes

Reaction equation

HRID 1911727 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH2:8]([NH2:10])[CH3:9].C(N(CC)CC)C>C(Cl)Cl>[CH2:8]([NH:10][C:5]([CH:1]1[CH2:4][CH2:3][CH2:2]1)=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chloride

Product 1

HCID 21691262HCID 21691262, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

Cyclobutanecarbonyl chloride (4.0 mL, 35 mmol) was added slowly to an ice-cooled solution of ethylamine [20 mL, 2M solution in tetrahydrofuran (THF)] and triethylamine (4.85 mL, 35 mmol) in anhydrous methylene chloride (25 mL) at 0-5° C. under nitrogen. After stirring for 20 min the mixture was warmed to 20-25° C. and stirred for an additional 5-7 h. The reaction was quenched by pouring the mixture into 5-10% aqueous sodium bicarbonate. The organic layer was separated, washed with brine, dried over sodium sulfate, and the solvent was evaporated to give cyclobutanecarboxylic acid ethylamide as a pale yellow liquid, which solidified upon standing at RT.

Workup

  1. stirringstirred for an additional 5-7 h
  2. customThe reaction was quenched
  3. additionby pouring the mixture into 5-10% aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3ccc027ebf1f4d2ab425a5b22c1bf398
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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