Dicyclohexylamine → HCID 22117430, compound

HRID 849899Notes

Reaction equation

HRID 849899 reaction equation
[CH3:1][C:2]1[C:3]([S:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:41])=O>ClCCl>[CH3:1][C:2]1[C:3]([S:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([Cl:41])=[O:22])=[CH:19][CH:18]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 30259184-[(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)sulfanyl]benzoic acid

Product 1

HCID 22117430HCID 22117430, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.4 g (4 mmol) of 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylthio)benzoic acid in 100 ml of anhydrous dichloromethane was introduced into a round-bottomed flask, 900 μl (4.4 mmol) of dicyclohexylamine were added and the mixture was stirred for one hour. Next, 320 μl (4.4 mmol) of thionyl chloride were added and the mixture was stirred for one hour. The reaction medium was evaporated to dryness, taken up in anhydrous ethyl ether, the dicyclohexylamine salt filtered off and the filtrate evaporated. 1.5 g (100%) of the crude acid chloride was recovered which was used as such in the continuation of the synthesis to follow.

Workup

  1. stirringthe mixture was stirred for one hour
  2. customThe reaction medium was evaporated to dryness
  3. filtrationthe dicyclohexylamine salt filtered off
  4. customthe filtrate evaporated
  5. custom1.5 g (100%) of the crude acid chloride was recovered which
  6. customsuch in the continuation of the synthesis

Sources & evidence

ORD record
ord-9eb5a1fb96a2480f94162004cbd7e371
Source dataset
uspto-grants-2000_01
Patent number
US06015569

Reaction notes

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