3-Methylbenzenesulphonyl chloride → HCID 9820889, compound

HRID 1018481Notes

Reaction equation

HRID 1018481 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:13][CH:14]1[CH:19]=[C:18]([CH3:20])[CH:17]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[O:16][NH:15]1>C(#N)C.C(Cl)(Cl)Cl>[CH3:13][CH:14]1[CH:19]=[C:18]([CH3:20])[CH:17]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[O:16][N:15]1[S:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 27345953-Methylbenzenesulphonyl chlorideHCID 18401525HCID 18401525, compound

Product 1

HCID 9820889HCID 9820889, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-methylbenzenesulphonyl chloride (0.075 mmol) in acetonitrile (1.5 ml) was added a solution of 3,6-dihydro-3,5-dimethyl-6-(4-methoxyphenyl)-2H-1,2-oxazine hydrochloride(0.403 mmol) in chloroform (0.5 ml) followed by poly(4-vinyl)pyridine (53 mg). The mixture was shaken at room temperature for 24 h then added polystyrene (co-divinylbenzene)amino methylated (100 mg) and the mixture shaken at room temperature for a further 24 h. The mixture was then filtered and the resin washed twice with chloroform. The filtrate was evaporated to give 3,6-dihydro-3,5-dimethyl-6-(4-methoxyphenyl)-2-(3-methylbenzenesulphonyl)-2H-1,2-oxazine as an oil. 1H NMR (CDCl3)δ 1.56(3H, d), 2.39(3H, s), 3.82(3H, s) 4.49(1H, m), 5.20(1H, s), 5.69(1H, d), 6.81(2H, d), 7.11(2H, d), 7.34(2H, m), 7.67(2H, d)

Workup

  1. stirringthe mixture shaken at room temperature for a further 24 h
  2. filtrationThe mixture was then filtered
  3. washthe resin washed twice with chloroform
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-012fcf5073254935b1a2b72f32845d44
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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