Dicyclohexylamine → HCID 57123062, compound

HRID 482506Notes

Reaction equation

HRID 482506 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:24]#[C:25][C:26]4[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[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:50])=O>ClCCl>[C:1]12([C:11]3[CH:12]=[C:13]([C:24]#[C:25][C:26]4[CH:34]=[CH:33][C:29]([C:30]([Cl:50])=[O:31])=[CH:28][CH:27]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[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 15289366HCID 15289366, compound

Product 1

HCID 57123062HCID 57123062, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.14 g (6.8 mmol) of 4-[3-(1-adamantyl)-4-methoxyethoxymethoxyphenylethynyl]benzoic acid in 100 ml of anhydrous dichloromethane was introduced into a round-bottomed flask, 1.4 ml (6.8 mmol) of dicyclohexylamine was added and stirring was carried out for one hour. 500 μl (6.8 mmol) of thionyl chloride were then added and stirring was carried out for one hour. Evaporation was carried out to dryness, the residue was taken up in anhydrous ethyl ether, the dicyclohexylamine salt was filtered and the filtrate was evaporated. 3.3 g (100%) of the crude acid chloride were collected, which chloride was used as is in the continuation of the synthesis to follow.

Workup

  1. stirringstirring
  2. waitwas carried out for one hour
  3. customEvaporation
  4. filtrationthe dicyclohexylamine salt was filtered
  5. customthe filtrate was evaporated
  6. custom3.3 g (100%) of the crude acid chloride were collected
  7. customas is in the continuation of the synthesis

Sources & evidence

ORD record
ord-fa3050c14cc94e8099c9d48114509f4d
Source dataset
uspto-grants-1998_08
Patent number
US05798354

Reaction notes

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