Dimethyl Sulfide → HCID 86697530, compound

HRID 626838Notes

Reaction equation

HRID 626838 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([CH:19]([OH:21])[CH3:20])[C:5]([O:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH:22]=C)[C:3]=1[C:24]#[N:25].[O:26]=[O+][O-].CSC>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[C:17]([CH:19]([OH:21])[CH3:20])[C:5]([O:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[C:4]([CH:22]=[O:26])[C:3]=1[C:24]#[N:25]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 86697529Tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate

Product 1

HCID 86697530HCID 86697530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate (1.6 g, 4.4 mmol) was dissolved in methylene chloride (1.2 mL) cooled in a dry ice acetone bath and ozone/oxygen was bubbled through the solution until a persistent blue color remained. The reaction was purged with oxygen and nitrogen to remove excess ozone and dimethyl sulfide (0.80 mL, 11 mmol) was added to reduce the ozonide. After stirring for 1 h, the reaction was complete. This was concentrated in vacuo to give a residue give tert-butyl {2-[4-chloro-3-cyano-2-formyl-6-(1-hydroxyethyl)phenoxy]ethyl}carbamate. LCMS calculated for C17H21ClN2O5Na (M+Na)+: m/z=391.1; found: 391.1.

Workup

  1. temperaturecooled in a dry ice acetone bath
  2. customozone/oxygen was bubbled through the solution until a persistent blue color
  3. customThe reaction was purged with oxygen and nitrogen
  4. additionwas added
  5. concentrationThis was concentrated in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-e212cd4a1976447f86e89094e55f1fff
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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