Sulfuric Acid → HCID 69794577, compound

HRID 416119Notes

Reaction equation

HRID 416119 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:3]=1[CH2:4][S:5][CH:6]1[CH2:11][CH2:10][CH2:9][C:8](=[N:12]O)[CH2:7]1.C1(C)C(S(Cl)(=O)=[O:27])=CC=CC=1.S(=O)(=O)(O)O.C(Cl)Cl>N1C=CC=CC=1>[CH3:1][C:2]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:3]=1[CH2:4][S:5][CH:6]1[CH2:11][CH2:10][CH2:9][NH:12][C:8](=[O:27])[CH2:7]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 8623o-Toluenesulfonyl chlorideHCID 85871177HCID 85871177, compound

Product 1

HCID 69794577HCID 69794577, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 828 mg of 3-(R/S)-(2,4,6-trimethyl-benzyl-sulfanyl)-cyclohexanone-oxime and 570 mg of toluenesulfonylchloride in 5 ml of pyridine is stirred at RT for 4 hours and additional 2 hours at 60°. The mixture obtained is distributed between diluted sulfuric acid (2 ml H2SO4 conc. in 15 ml H2O) and CH2Cl2, the organic phase obtained is dried, solvent is evaporated and the evaporation residue is subjected to chromatography. 4-(R/S)-(2,4,6-Trimethyl-benzyl-sulfanyl)-azepan-2-one is obtained. 1H-NMR(d-6-DMSO): 7.5 (m,1H,NHCO), 6.8 (s,2H,arom.H), 3.75 (s,2H,C6H5CH2S—),3.2 (m, 1H,CHN), 3.1(m,3H, CH2NH,CHS) AB-system: νA=2.72,νB=2.65( 2H,CH2C═O, J=13.4 Hz, J=4.5 Hz) 2.13 2.15,2.3(9H, 3×CH3)

Workup

  1. customThe mixture obtained
  2. customthe organic phase obtained
  3. customis dried
  4. customsolvent is evaporated

Sources & evidence

ORD record
ord-3461f0a620d749b9991b1e14292d9d96
Source dataset
uspto-grants-2012_01
Patent number
US08088823B2

Reaction notes

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