Water → HCID 18319519, compound

HRID 1699397Notes

Reaction equation

HRID 1699397 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][C:6]=2[CH:17]=1.[CH3:18][S:19]SC.C(OCC)(=O)C.O>C(#N)C>[CH3:18][S:19][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12232Dimethyl DisulfideHCID 18319622HCID 18319622, compound

Product 1

HCID 18319519HCID 18319519, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of ethyl 2,3-dihydro-7-amino-1-benzoxepin-4-carboxylate (2.0 g), dimethyl disulfide (2.3 ml) and t-butylnitrile (1.2 ml) in acetonitrile (4 ml) was stirred at 50° C. for 2.5 hours. The mixture was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of hexane and toluene (1:1) as an eluent. The eluted fractions containing the desired product were collected and evaporated in vacuo to give ethyl 2,3-dihydro-7-methylthio-1-benzoxepin-4-carboxylate (1.24 g).

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of hexane and toluene (1:1) as an eluent
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-373bff12358e4be6bda83cc70755305c
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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