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

HRID 1018475Notes

Reaction equation

HRID 1018475 reaction equation
C([Cl:4])(=O)C.Cl.C(OC([N:13]1[CH:18]([CH3:19])[CH:17]=[C:16]([CH3:20])[CH:15]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=2)[O:14]1)=O)(C)(C)C>CO>[ClH:4].[CH3:19][CH:18]1[CH:17]=[C:16]([CH3:20])[CH:15]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH3:29])=[CH:25][CH:26]=2)[O:14][NH:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 184015392-t-butoxycarbonyl-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Acetyl chloride (30 ml) was added dropwise over 10 mins to a cooled solution of methanol (300 ml) The resulting solution of hydrogen chloride in methanol was added to a stirred solution of 2-t-butoxycarbonyl-3, 6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1, 2-oxazine (11.6 g, 34.8 mmol) in methanol (50 ml). After 4 h at room temperature the mixture was evaporated to a solid (8.35 g), triturated with diethyl ether and the solid filtered to give 3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine hydrochloride.

Workup

  1. customAfter 4 h at room temperature the mixture was evaporated to a solid (8.35 g)
  2. customtriturated with diethyl ether
  3. filtrationthe solid filtered

Sources & evidence

ORD record
ord-6dc271ae0152468a8254b5287a65bc5e
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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