Benzhydrol → 2-[(Diphenylmethyl)sulfanyl]ethan-1-amine

HRID 652750Notes

Reaction equation

HRID 652750 reaction equation
Cl.[SH:2][CH2:3][CH2:4][NH2:5].[C:6]1([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(C(O)=O)(F)(F)F>[C:6]1([CH:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[S:2][CH2:3][CH2:4][NH2:5])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7037BenzhydrolHCID 9082Cysteamine Hydrochloride

Product 1

HCID 2794132-[(Diphenylmethyl)sulfanyl]ethan-1-amine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 2-mercaptoethylamine hydrochloride (12.058 g, 0.106 mol) and diphenylmethanol (20.062 g, 0.109 mol) in CF3CO2H (180 ml) was stirred at room temperature for 5.5 hours, then evaporated to a brownish/orange oil. Ether (500 ml) and 2N NaOH (200 ml) were added. The ether layer was washed with water (3×100 ml), saturated aqueous NaCl (100 ml), dried (MgSO4) and most of the ether removed in vacuo. The solution was cooled to -10° giving white crystalline compound (XXVI). This material was filtered, washed with cold ether and dried in vacuo (18.323 g, 71%). The volume of the combined washing and filtrate was reduced and cooled (-10° C.) giving a second crop, combined yield 20.479 g (84%), mp 74° .

Workup

  1. customevaporated to a brownish/orange oil
  2. additionEther (500 ml) and 2N NaOH (200 ml) were added
  3. washThe ether layer was washed with water (3×100 ml), saturated aqueous NaCl (100 ml)
  4. dry with materialdried (MgSO4)
  5. custommost of the ether removed in vacuo
  6. temperatureThe solution was cooled to -10°

Sources & evidence

ORD record
ord-24d9f3a0bf114aaeba86cb7dfcb38fc8
Source dataset
uspto-grants-1987_06
Patent number
US04673562

Reaction notes

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