1-Chloro-1-nitrosocyclohexane → 3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine hydrochloride

HRID 1018472Notes

Reaction equation

HRID 1018472 reaction equation
[Cl:1]C1([N:8]=[O:9])CCCCC1.[CH2:10]([O:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[C:20](\[CH3:24])/[CH:21]=[CH:22]/[CH3:23])=[CH:15][CH:14]=1)[CH3:11]>C(O)C.C(OCC)C>[ClH:1].[CH3:23][CH:22]1[CH:21]=[C:20]([CH3:24])[CH:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:10][CH3:11])=[CH:14][CH:15]=2)[O:9][NH:8]1

Participants

5

Reactant 2

HCID 6375621-Chloro-1-nitrosocyclohexaneHCID 184015281-(4-ethoxyphenyl)-2-methylpent-1E,3E-diene

Product 1

HCID 184015323,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1-chloro-1-nitrosocyclohexane (3.22 g, 21.86 mmol) in ethanol (2.31 ml) and diethyl ether (8 ml) cooled in an ice bath was added a solution of 1-(4-ethoxyphenyl)-2-methylpent-1E,3E-diene (4.0 g, 19.88 mmol) in diethyl ether (4 ml). The reaction vessel was sealed and kept in a fridge at 0° C. over a period of 4 weeks yielding three crops of 3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine hydrochloride as white crystals.

Workup

  1. customThe reaction vessel was sealed
  2. waitkept in a fridge at 0° C. over a period of 4 weeks

Sources & evidence

ORD record
ord-ccf11d06ccc0423e853f61923516b0c0
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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