Triethylamine → HCID 11456665, compound

HRID 1748147Notes

Reaction equation

HRID 1748147 reaction equation
[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:8][CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH2:13]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28]1([C:34]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[S:35][CH2:36][CH2:37][NH2:38])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>ClCCl>[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:8][CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH2:13][NH:38][CH2:37][CH2:36][S:35][C:34]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 262764S-TritylcysteamineHCID 58040950HCID 58040950, compound

Product 1

HCID 11456665HCID 11456665, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve N-[2-((Triphenylmethyl)thio)ethyl]-chloroacetamide (5.4 g, 13.8 mmol) and 2-[(triphenylmethyl)thio]ethylamine (4.4 g, 13.8 mmol) in 100 mL dichloromethane, then add triethylamine (3.0 mL, 20.8 mmol) into the solution, heat and reflux for 48 hours. After being cooled, wash with 100 mL sodium bicarbonate aqueous solution (NaHCO3) and take the organic layer. After being dried with anhydrous sodium sulfate and concentrated, liquid chromatography (silicon dioxide, ethyl acetate hexane=1:1) is used for separation and purification so as to get light yellow oil product

Workup

  1. temperaturereflux for 48 hours
  2. temperatureAfter being cooled
  3. washwash with 100 mL sodium bicarbonate aqueous solution (NaHCO3)
  4. dry with materialAfter being dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customliquid chromatography (silicon dioxide, ethyl acetate hexane=1:1) is used for separation and purification so as
  7. customto get light yellow oil product

Sources & evidence

ORD record
ord-3ddc9f2d77f045a6a14e0b36cbc6ab3e
Source dataset
uspto-grants-2015_10
Patent number
US09150602B2

Reaction notes

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