Dimethyl Sulfide → HCID 69061372, compound

HRID 1436876Notes

Reaction equation

HRID 1436876 reaction equation
[C:1]([C:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:16][CH:17]=C)[CH2:4][C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:6])#[N:2].CSC>C(Cl)Cl>[C:1]([C:3]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:17][N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[C:5](=[O:6])[CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 69065113HCID 69065113, compound

Product 1

HCID 69061372HCID 69061372, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a cooled (−78° C.) solution of 3-cyano-N-(4-fluorobenzyl)-3-phenylhex-5-enamide (8.00 g, 24.8 mmol) in CH2Cl2 (500 mL) was bubbled ozone until a blue color persisted. The mixture was stirred for 10 min, then dimethyl sulfide (84.6 g, 1.36 mol) was added. After stirring for 48 hours at room temperature, the mixture was concentrated under vacuum. The residue was partitioned between EtOAc and water. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum. The residual material was purified using silica gel column chromatography eluting with 0-40% EtOAc in hexanes. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.45 (m, 5H), 7.29 (m, 2H), 7.15 (t, J=8.9 Hz, 2H), 6.78 (d, J=7.7 Hz, 1H), 5.50 (d, J=7.7 Hz, 1H), 4.72 (s, 2H), 3.17 (q, J=16 Hz, 2H) ppm. ES MS M+1=307.

Workup

  1. customwas bubbled ozone until a blue color
  2. stirringAfter stirring for 48 hours at room temperature
  3. concentrationthe mixture was concentrated under vacuum
  4. customThe residue was partitioned between EtOAc and water
  5. extractionThe organic extract
  6. dry with materialwas dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residual material was purified
  10. washeluting with 0-40% EtOAc in hexanes
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ed00503b741148658feb34e95ec3f5c4
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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