Dicyclohexylamine → 4-But-2-ynyloxybenzoyl chloride

HRID 517488Notes

Reaction equation

HRID 517488 reaction equation
C1(NC2CCCCC2)CCCCC1.[CH2:14]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)[C:15]#[C:16][CH3:17].S(Cl)([Cl:30])=O>ClCCl>[CH2:14]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([Cl:30])=[O:24])=[CH:21][CH:20]=1)[C:15]#[C:16][CH3:17]

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 222825564-But-2-ynyloxy-benzoic acid

Product 1

HCID 593240144-But-2-ynyloxybenzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 ml (14.2 mmol) of dicyclohexylamine are added to a solution of 2.7 g (14.2 mmol) of 4-but-2-ynyloxybenzoic acid diluted in 30 ml of dichloromethane. After stirring for 30 min at ambient temperature, the reaction medium is cooled to 0° C. and 1.0 ml (14.2 mmol) of thionyl chloride is slowly added. The mixture is then stirred at ambient temperature for 1 h 30 min, then the dicyclohexylamine salts are precipitated by adding 50 ml of diethyl ether. After filtration of the reaction medium, the filtrate is concentrated under vacuum. 2.9 g (100%) of 4-but-2-ynyloxybenzoyl chloride are obtained in the form of a brown solid.

Workup

  1. temperaturethe reaction medium is cooled to 0° C.
  2. stirringThe mixture is then stirred at ambient temperature for 1 h 30 min
  3. customthe dicyclohexylamine salts are precipitated
  4. additionby adding 50 ml of diethyl ether
  5. filtrationAfter filtration of the reaction medium
  6. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-29f7082b7c774bd0838ef479228189b9
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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