Chloroacetyl chloride → HCID 58040950, compound

HRID 1748146Notes

Reaction equation

HRID 1748146 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:31][CH2:32][C:33](Cl)=[O:34]>ClCCl.C(Cl)(Cl)Cl>[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[S:8][CH2:9][CH2:10][NH:11][C:33](=[O:34])[CH2:32][Cl:31])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 8471TriethylamineHCID 262764S-Tritylcysteamine

Product 1

HCID 58040950HCID 58040950, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-[(triphenylmethyl)thio]ethylamine (5.24 g, 16.4 mmol) and triethylamine (2.76 mL, 19.6 mmol) in 150 mL dichloromethane. Chloroacetyl chloride (1.56 mL, 19.6 mmol) is dissolved in 20 mL chloroform. Being cooled down with an ice bath, slowly drop chloroacetyl chloride into the solution. Then stir the solution at room temperature for 2 hours. Next wash organic phase with followings in turn: 2N hydrochloric acid solution (120 mL), and saturated sodium bicarbonate aqueous solution (100 mL). The organic phase is dehydrated by anhydrous sodium sulfate (Na2SO4) and then is concentrated in vacuo to yield yellow oily N-[2-((Triphenylmethyl)thio) ethyl]-chloroacetamide (5.62 g, 86.6%).

Workup

  1. temperatureBeing cooled down with an ice bath
  2. washNext wash organic phase with followings in turn
  3. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-511611c65bcc48019eb6b00a3d7edc80
Source dataset
uspto-grants-2015_10
Patent number
US09150602B2

Reaction notes

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