Pyridine → O-2-[4-(1-methylpropoxy)phenoxy]ethyl N-ethyl-N-phenylsulfenylcarbamate

HRID 2309845Notes

Reaction equation

HRID 2309845 reaction equation
[CH2:1]([NH:3][C:4](=[O:20])[O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:19])[CH2:17][CH3:18])=[CH:11][CH:10]=1)[CH3:2].N1C=CC=CC=1.[C:27]1([S:33]Cl)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH2:1]([N:3]([S:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:4](=[O:20])[O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:16]([CH3:19])[CH2:17][CH3:18])=[CH:13][CH:14]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11008040Benzenesulfenyl chlorideHCID 13939036HCID 13939036, compound

Product 1

HCID 20184898O-2-[4-(1-methylpropoxy)phenoxy]ethyl N-ethyl-N-phenylsulfenylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To O-2-[4-(1-methylpropoxy)phenoxy]ethyl N-ethylcarbamate (1.50 g, 5.34 mmol) and pyridine (1 ml, 11.75 mmol) in 20 ml of methylene chloride at RT is added phenylsulfenyl chloride (1.54 g, 10.70 mmol). The reaction mixture is stirred for 2 hours, after which it is poured into ice water and extracted with ether. The combined organic layers are washed with 10% HCl, with water until neutral and with brine and dried. After filtration and removal of the solvent, the product is purified by prep. TLC to give O-2-[4-(1-methylpropoxy)phenoxy]ethyl N-ethyl-N-phenylsulfenylcarbamate, MS m/e 390 (M+ +H) (compound 23, Table A).

Workup

  1. extractionextracted with ether
  2. washThe combined organic layers are washed with 10% HCl, with water until neutral and with brine
  3. customdried
  4. filtrationAfter filtration and removal of the solvent
  5. customthe product is purified by prep

Sources & evidence

ORD record
ord-d61eb89af2f14d639aa6e6a2893542b7
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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