Triphenylcarbinol → S-Tritylcysteamine

HRID 1748145Notes

Reaction equation

HRID 1748145 reaction equation
[CH2:1]([NH2:4])[CH2:2][SH:3].Cl.[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(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:6]1([C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[S:3][CH2:2][CH2:1][NH2:4])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6457TriphenylcarbinolHCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 262764S-TritylcysteamineYield 103.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 2-thioethylamine hydrochloride (5 g, 44.2 mmol), triphenylmethanol (11 g, 42.5 mmol) and triethylamine (7 mL, 49.9 mmol) in 100 mL chloroform. Heat and reflux until the solution temperature reaches a certain temperature, slowly drop a catalyst borontrifluoride ethyl ether complex (15 mL, 119.5 mmol) into the solution and continue heating and reflux for 4 hours. Then cool down, add sodium bicarbonate aqueous solution into the solution and stir the mixture. White solid product is precipitated out immediately. Get the solid by suction filtration, wash the solid with water, and dry the solid. Thus solid product 2-[(triphenylmethyl)thio]ethylamine (14.0 g, 99%) is obtained.

Workup

  1. temperatureHeat
  2. temperaturereflux until the solution temperature
  3. temperaturecontinue heating
  4. temperaturereflux for 4 hours
  5. temperatureThen cool down
  6. customWhite solid product is precipitated out immediately
  7. customGet the solid
  8. filtrationby suction filtration
  9. washwash the solid with water
  10. customdry the solid

Sources & evidence

ORD record
ord-a2545e21e3d44f26aae026364c07b85d
Source dataset
uspto-grants-2015_10
Patent number
US09150602B2

Reaction notes

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