Sulfuric Acid → HCID 69794577, compound

HRID 1711203Notes

Reaction equation

HRID 1711203 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: vA=2.72,vB=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-52b85908ad544570b7af5d9ea565ff45
Source dataset
uspto-grants-2010_09
Patent number
US07790749B2

Reaction notes

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