Tert-Butyl nitrite → Sulfide, nitroso trityl

HRID 1637578Notes

Reaction equation

HRID 1637578 reaction equation
[C:1]1([C:7]([SH:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:21](OC(C)(C)C)=[O:22]>C(Cl)Cl>[N:21]([S:20][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:22]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-

Product 1

HCID 95186Sulfide, nitroso tritylYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triphenylmethyl mercaptan (0.050 g, 0.18 mmol) was dissolved in anhydrous methylene chloride and cooled to 0° C. Tert-butyl nitrite (0.186 g, 1.80 mmol) was added and the resulting mixture was stirred at 0° C. for 30 min. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 1 hour. The solvent and excess of tert-butyl nitrite were evaporated to give the title compound as a green solid (0.054 g, 98%). 1H NMR (CDCl3) δ: 7.13-7.18 (m, 4 H), 7.25-7.39 (m, 11⌴H).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 1 hour
  3. customThe solvent and excess of tert-butyl nitrite were evaporated

Sources & evidence

ORD record
ord-370a03af503242e38fd938483437012a
Source dataset
uspto-grants-2000_03
Patent number
US06043233

Reaction notes

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