Ethanol → HCID 66672783, compound

HRID 352171Notes

Reaction equation

HRID 352171 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1.[CH2:15](O)[CH3:16]>>[ClH:3].[NH2:5][CH:6]1[CH2:11][CH2:10][C:9]([CH2:15][CH3:16])([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 1715604-Aminocyclohexanecarboxylic acid

Product 1

HCID 66672783HCID 66672783, compound

Procedure

Thionyl chloride (2.55 mL, 35 mmol) was added dropwise to absolute ethanol (100 mL) under a N2 atmosphere. The resulting solution was stirred at room temperature for 10 min then 4-amino-1-cyclohexanecarboxylic acid (4.29 g, 30 mmol, cis, trans mixture) was added as a solid. The resulting solution was stirred at room temperature overnight. The solvent was removed in vacuo, the residue dissolved in ethanol (25 mL) and this solution was slowly added to a flask containing rapidly stirred ether (700 mL). The precipitate that formed was collected by filtration and dried in vacuo to give 5.75 g, 92% as a white solid. MS (ion spray) 172 (M+1).

Workup

  1. stirringThe resulting solution was stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in ethanol (25 mL)
  4. additionthis solution was slowly added to a flask
  5. additioncontaining rapidly stirred ether (700 mL)
  6. customThe precipitate that formed
  7. filtrationwas collected by filtration
  8. customdried in vacuo
  9. customto give 5.75 g, 92% as a white solid

Sources & evidence

ORD record
ord-e5e95f6eeb264a658c26157bef3f9ae0
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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