Hydrochloric Acid → ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

HRID 2178221Notes

Reaction equation

HRID 2178221 reaction equation
C([N:4]1[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[CH:11][C:12]([C:14]3[S:15][C:16]([N:24]([CH3:34])[CH2:25][CH2:26][O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=3)=[CH:13][C:5]1=2)(=O)C.C(O)C.Cl.C(=O)(O)[O-].[Na+]>CCOC(C)=O>[O:7]1[CH2:8][CH2:9][NH:4][C:5]2[CH:13]=[C:12]([C:14]3[S:15][C:16]([N:24]([CH3:34])[CH2:25][CH2:26][O:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=3)[CH:11]=[CH:10][C:6]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 59418712ethyl 2-(4-acetyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

Product 1

HCID 59418724ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To ethyl 2-(4-acetyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20A) (0.102 g, 0.212 mmol) was added ethanol (4 mL) and 6N HCl (6 mL). The reaction mixture was allowed to heat to 60° C. and stir for 8 hours. The reaction was allowed to cool to rt. To the reaction mixture was added EtOAc and saturated sodium bicarbonate. The layers were separated and extracted with EtOAc and the combined organic extracts were washed sequentially with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to provide 0.079 g (85%) of the desired product ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20B): LC/MS (APCI): m/z 440.1 (M+H).

Workup

  1. temperatureto cool to rt
  2. customThe layers were separated
  3. extractionextracted with EtOAc
  4. washthe combined organic extracts were washed sequentially with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f9ef099a86549d593cc5e1f07576c4a
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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