Triethylamine → Benzyl 2-(4-methoxyphenylthio)ethylcarbamate

HRID 532123Notes

Reaction equation

HRID 532123 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>ClCCl.C1COCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH:12][C:21](=[O:22])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 12261932Ethanamine, 2-[(4-methoxyphenyl)thio]-

Product 1

HCID 57864669Benzyl 2-(4-methoxyphenylthio)ethylcarbamateYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

To the solution of compound 1 (10 g, 54.6 mmol) and triethylamine (15 mL, 106 mmol) in 200 mL of dichloromethane was added benzyl chloroformate (7.24 mL, 51.5 mmol, diluted in 100 mL of dichloromethane) dropwise at 0° C. After the addition, the solution was stirred at r.t. for one hour. The solid was removed by filtration. The solution was extracted with 100 mL of 0.1 M HCl and 100 mL of sat. sodium carbonate, and dried over anhydrous sodium sulfate. Removal of solvent provided a white solid that was stirred in 200 mL of THF/hexane (1:20) for three hours. The solid was collected by filtration to give 14.2 g of the target compound in 87% yield.

Workup

  1. additionAfter the addition
  2. customThe solid was removed by filtration
  3. extractionThe solution was extracted with 100 mL of 0.1 M HCl and 100 mL of sat. sodium carbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of solvent
  6. customprovided a white solid
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-8b855148b43f4ee78f9ccecbd86fc660
Source dataset
uspto-grants-2014_10
Patent number
US08853198B2

Reaction notes

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