Triphenylcarbinol → S-Tritylcysteamine

HRID 1830503Notes

Reaction equation

HRID 1830503 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[C:6]1([C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([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:12]([S:5][CH2:4][CH2:3][NH2:2])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 6457TriphenylcarbinolHCID 9082Cysteamine Hydrochloride

Product 1

HCID 262764S-TritylcysteamineYield 85.2%

Procedure

2-Aminoethanethiol hydrochloride (1.0 g, 8.6 mmol) was dissolved in acetic trifluoride (10 ml) and added with triphenylmethanol (2.32 g, 8.6 mmol). The resulting solution was stirred at room temperature for 1 hr and concentrated by distilling under reduced pressure. The filtrate was diluted with ethyl acetate (50 ml) and washed with 3 M sodium hydroxide aqueous solution, water, saturated sodium bicarbonate aqueous solution, saturated sodium chloride aqueous solution in sequence. The organic phase was dried over anhydrous sodium sulfate and distilled under reduced pressure to obtain a white solid of 2-(tritylsulfanyl)-1-ethaneamine (2.32 g, 7.3 mmol, 85.2%).

Workup

  1. concentrationconcentrated
  2. distillationby distilling under reduced pressure
  3. additionThe filtrate was diluted with ethyl acetate (50 ml)
  4. washwashed with 3 M sodium hydroxide aqueous solution, water, saturated sodium bicarbonate aqueous solution, saturated sodium chloride aqueous solution in sequence
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-be84a38b97764787a00955bbcddbf676
Source dataset
uspto-grants-2006_06
Patent number
US07067508B2

Reaction notes

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