Dichloromethane → N-triphenylmethyl-2-methylaminocarbonylthioethylamine

HRID 1607104

Reaction equation

HRID 1607104 reaction equation
CS[N:3]=[C:4]=[O:5].[C:6]1([C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:13][CH2:14][CH2:15][SH:16])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[CH2:30]Cl>>[C:6]1([C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:13][CH2:14][CH2:15][S:16][C:4]([NH:3][CH3:30])=[O:5])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 15616512N-triphenylmethylcysteamineHCID 21933440Methylthioisocyanate

Product 1

HCID 15616514N-triphenylmethyl-2-methylaminocarbonylthioethylamineYield 79%

Procedure

Methylthioisocyanate (210 mg) was dissolved in anhydrous dichloromethane (5 ml). To the solution were added N-triphenylmethylcysteamine (1.00 g: 1.1 molar equivalent) while cooling with ice. The reaction solution was stirred at room temperature for 30 minutes and was concentrated under reduced pressure. The residue was dissolved in chloroform (50 ml) and well washed with water and a saturated solution of sodium chloride. The chloroform layer was dried by using anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chroomatography using a solvent system of hexane/ethyl acetae (5:1 v/v) to obtain the desired substance (0.89 g) with a yield of 79%.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform (50 ml)
  4. washwell washed with water
  5. dry with materialThe chloroform layer was dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chroomatography
  8. customto obtain the desired substance (0.89 g) with a yield of 79%

Sources & evidence

ORD record
ord-690d4af0d04b4717bcf099b7abfd8a19
Source dataset
uspto-grants-1989_09
Patent number
US04863935

Linked notes

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