1,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate → 1,1-dimethylethyl 2-thioxo-2,3,5,6,8,9-hexahydro-7H-[1,3]oxazolo[4,5-h][3]benzazepine-7-carboxylate

HRID 1668574Notes

Reaction equation

HRID 1668574 reaction equation
[NH2:1][C:2]1[C:19]([OH:20])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C(O[C:24](SC(OCC)=S)=[S:25])C.[K]>N1C=CC=CC=1.C(OCC)(=O)C>[S:25]=[C:24]1[NH:1][C:2]2[C:19](=[CH:18][C:5]3[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=3[CH:3]=2)[O:20]1

Participants

5

Reactant 2

HCID 591504721,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateHCID 86638054HCID 86638054, compound

Product 1

HCID 591505171,1-dimethylethyl 2-thioxo-2,3,5,6,8,9-hexahydro-7H-[1,3]oxazolo[4,5-h][3]benzazepine-7-carboxylateYield 69.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (3.6 mmol) and potassium [(ethyloxy)carbonothioyl]sulfide (3.96 mmol) were suspended in pyridine (6 ml) and the reaction mixture was heated at 70° C. for 3 h. The solvent was removed under reduced pressure providing a crude product that after dissolution in ethyl acetate, washing with water and evaporation of the organic phase under reduced pressure gave the title compound as a yellow solid (2.5 mmol, 69% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customproviding a crude product that
  3. washwashing with water and evaporation of the organic phase under reduced pressure

Sources & evidence

ORD record
ord-456ef6d6316c4ca5b1b551c7b9244f70
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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