Hydrogen chloride-ethyl acetate → 8-(3-Methoxyphenyl)-2-methyl-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepine

HRID 1404972Notes

Reaction equation

HRID 1404972 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[O:16][CH:15]([CH3:18])[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][C:11]=2[S:10][CH:9]=1.[C:26](OCC)(=[O:28])C.Cl>>[CH3:26][O:28][C:5]1[CH:4]=[C:3]([C:8]2[C:17]3[O:16][CH:15]([CH3:18])[CH2:14][NH:13][CH2:12][C:11]=3[S:10][CH:9]=2)[CH:2]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67959376HCID 67959376, compound

Product 1

HCID 679591608-(3-Methoxyphenyl)-2-methyl-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepineYield 95%

Procedure

tert-Butyl 8-(2-fluorophenyl)-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (168 mg) was stirred in 4 N hydrogen chloride-ethyl acetate solution (5 mL) for 30 min. The reaction solution was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to give 8-(2-fluorophenyl)-2-methyl-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepine 1 hydrochloride (132 mg, 95%) as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-803439d2077743758c701ebc1519f4dc
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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