Dicyclohexylamine → 4-[3-(1-Adamantyl)-4-methoxybenzoylthio]benzoic acid chloride

HRID 1681573Notes

Reaction equation

HRID 1681573 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=3[O:29][CH3:30])[C:14]([S:16][C:17]3[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:46])=O>ClCCl>[C:1]12([C:11]3[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=3[O:29][CH3:30])[C:14]([S:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([Cl:46])=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 233627344-[3-(1-Adamantyl)-4-methoxybenzoylthio]benzoic acid

Product 1

HCID 543105854-[3-(1-Adamantyl)-4-methoxybenzoylthio]benzoic acid chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a round bottom flask there are introduced 3.80 g (9 mmoles) of 4-[3-(1-adamantyl)-4-methoxybenzoylthio]benzoic acid, 40 ml of dichloromethane and 1.8 ml (9 mmoles) of dicyclohexylamine. The reaction mixture is stirred for one hour. To the resulting solution 720 μl (9.9 mmoles) of thionylchloride are added and the mixture is stirred at ambient temperature for 2 hours. It is then evaporated to dryness, and taken up in 500 ml of ethyl ether. The dicyclohexylammonium chloride is filtered and the solvent is evaporated. 3.97 g (100% yield) of crude 4-[3-(1-adamantyl)-4-methoxybenzoylthio]benzoic acid chloride which is used as such for the following synthesis are obtained.

Workup

  1. stirringthe mixture is stirred at ambient temperature for 2 hours
  2. customIt is then evaporated to dryness
  3. filtrationThe dicyclohexylammonium chloride is filtered
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-f67fc24a1c674f079ba368288e948ff1
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

Loading…