Diethylamine → HCID 85604371, compound

HRID 1920494Notes

Reaction equation

HRID 1920494 reaction equation
[CH3:1][CH:2]([CH3:9])[CH2:3][CH:4]=[CH:5][C:6]([OH:8])=O.S(Cl)(Cl)=O.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>ClCCl.CN(C)C=O>[CH2:14]([N:16]([CH2:17][CH3:18])[C:6](=[O:8])[CH:5]=[CH:4][CH2:3][CH:2]([CH3:1])[CH3:9])[CH3:15]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 53421020HCID 53421020, compound

Product 1

HCID 85604371HCID 85604371, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
28.5 °C

Procedure

To a solution of 5-methylhex-2-enoic acid (formula-3) (20 grams) in dichloromethane (250 ml), 2 ml of dimethyl formamide was added. To this mixture thionyl chloride (24.1 grams) was added. The reaction mixture was stirred for 2.5 hours at 28-29° C. The reaction mixture was cooled to 0-5° C. and diethyl amine was added to the reaction mixture at 5-8° C. until the pH reached to 8.5. The reaction mixture was stirred for 1.5 hours at 0-5° C. The reaction mixture was quenched with water. Separated the aqueous and organic layers. The organic layer was washed with 5% sodium bicarbonate solution and was dried over anhydrous sodium sulphate. The solvent was distilled off completely under vacuum to provide the title compound as solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0-5° C.
  2. stirringThe reaction mixture was stirred for 1.5 hours at 0-5° C
  3. customThe reaction mixture was quenched with water
  4. customSeparated the aqueous and organic layers
  5. washThe organic layer was washed with 5% sodium bicarbonate solution
  6. dry with materialwas dried over anhydrous sodium sulphate
  7. distillationThe solvent was distilled off completely under vacuum

Sources & evidence

ORD record
ord-86e8700bcc074694aaa7c48f97eeb7be
Source dataset
uspto-grants-2012_05
Patent number
US08168828B2

Reaction notes

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