Thiophenol → HCID 70617595, compound

HRID 917975Notes

Reaction equation

HRID 917975 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Cl:9][CH2:10][CH:11]([OH:26])[CH2:12][N:13]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>[Na].C(O)C>[ClH:9].[OH:26][CH:11]([CH2:10][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:12][N:13]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 7969ThiophenolHCID 70617487HCID 70617487, compound

Product 1

HCID 70617595HCID 70617595, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 5360545SodiumSolvent

Procedure

One mol of thiophenol is dissolved in a solution of 46 g of sodium in ethanol. To the resulting solution there is progressively added 1 mol of an ethanolic solution of (3-chloro-2-hydroxy propyl) dicyclohexylamine hydrochloride. This mixture is then heated for two hours at reflux. After cooling the same, the reaction mixture is filtered and the filtrate evaporated to dryness. The resulting oily residue is taken up in sulfuric ether, through which there is then bubbled gaseous HCl. A white precipitate rapidly forms which is then filtered therefrom and recrystallized in ethanol for a 63 percent yield of white crystals melting at 181°C.

Workup

  1. temperatureThis mixture is then heated for two hours
  2. temperatureat reflux
  3. temperatureAfter cooling the same, the reaction mixture
  4. filtrationis filtered
  5. customthe filtrate evaporated to dryness
  6. filtrationA white precipitate rapidly forms which is then filtered

Sources & evidence

ORD record
ord-56921ab4890a4be08521271188cb6fb1
Source dataset
uspto-grants-1976_07
Patent number
US03968218

Reaction notes

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