Water → Acetamide, 2-bromo-N-[2-[(triphenylmethyl)thio]ethyl]-

HRID 1830504Notes

Reaction equation

HRID 1830504 reaction equation
[C:1]([S:20][CH2:21][CH2:22][NH2:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:31][CH2:32][C:33](Br)=[O:34].O>C(Cl)Cl>[C:1]([S:20][CH2:21][CH2:22][NH:23][C:33](=[O:34])[CH2:32][Br:31])([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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 262764S-Tritylcysteamine

Product 1

HCID 11259232Acetamide, 2-bromo-N-[2-[(triphenylmethyl)thio]ethyl]-Yield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(tritylsulfanyl)-1-ethaneamine (0.5 g, 1.6 mmol) was dissolved in methylene chloride (10 ml) and added with triethylamine (0.22 ml, 1.6 mmol). To the solution, bromoacetylbromide (0.14 ml, 1.6 mmol) in methylene chloride (1 ml) was added dropwise. The resulting solution was stirred at room temperature for 15 min and added with water (30 ml). The organic phase was washed with 1 M hydrogen chloride, water, saturated sodium bicarbonate aqueous solution, and 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 N1-(2(tritylsulfanyl)ethyl)-2-bromoacetamide (0.67 g, 1.51 mmol, 94.2%).

Workup

  1. washThe organic phase was washed with 1 M hydrogen chloride, water, saturated sodium bicarbonate aqueous solution, and saturated sodium chloride aqueous solution in sequence
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-d696a3e092654ee59086f30ca30a5e40
Source dataset
uspto-grants-2006_06
Patent number
US07067508B2

Reaction notes

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