Dicyclohexylamine → 3-Iodobenzoyl chloride

HRID 1384158Notes

Reaction equation

HRID 1384158 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:26])=O>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([Cl:26])=[O:6]

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 120603-Iodobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 743783-Iodobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 15 g (0.06 mol) of 3-iodobenzoic acid in 100 ml of anhydrous dichloromethane is introduced into a round-bottomed flask, 13 ml (0.063 mol) of dicyclohexylamine are added and the mixture is stirred for one hour. 4.6 ml (0.063 mol) of thionyl chloride are then added and the mixture is stirred for one hour. The mixture is evaporated to dryness, the residue is taken up in anhydrous ethyl ether, the dicyclohexylamine salt is filtered off and the filtrate is evaporated. 17 g (100%) of the crude acid chloride are collected, which product will be used without further purification for the rest of the synthesis.

Workup

  1. stirringthe mixture is stirred for one hour
  2. customThe mixture is evaporated to dryness
  3. filtrationthe dicyclohexylamine salt is filtered off
  4. customthe filtrate is evaporated
  5. custom17 g (100%) of the crude acid chloride are collected
  6. customwhich product will be used without further purification for the rest of the synthesis

Sources & evidence

ORD record
ord-8337bc7ee41f404dad6a886209dd9c51
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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