Diethyl Ether → HCID 15662568, compound

HRID 1073432Notes

Reaction equation

HRID 1073432 reaction equation
[CH3:1][CH:2]([S:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])=[CH:8][CH:7]=1)[CH2:3][CH3:4].I([O-])(=O)(=O)=[O:22].[Na+].CCOCC>CO.O>[CH3:1][CH:2]([S:5]([C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])=[CH:8][CH:7]=1)=[O:22])[CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14552619HCID 14552619, compoundHCID 23667635Sodium periodate

Product 1

HCID 15662568HCID 15662568, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of ethyl N-[4-(1-methylpropylthio)phenoxyethyl]carbamate (cpd. 40, from Example 13) (2.12 g, 7.1 mmol) in 7 ml of methanol at 0° is added, dropwise over 5 min., sodium metaperiodate (1.67 g, 7.8 mmol) in 13 ml of water. The mixture is stirred for 3 hours while warming to RT. The reaction is worked up by addition of water and extraction with ether. The combined organic extracts are washed with saturated sodium thiosulfate, with water and with brine, dried and the solvent is removed to give ethyl N-{2-[4-(1-methylpropylsulfinyl)phenoxy]ethyl}carbamate (compound 80, Table A).

Workup

  1. washThe combined organic extracts are washed with saturated sodium thiosulfate, with water and with brine
  2. customdried
  3. customthe solvent is removed

Sources & evidence

ORD record
ord-91cba408ff9941eea803ca0f06a832c2
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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