Sodium Hydroxide → HCID 59150481, compound

HRID 1668583Notes

Reaction equation

HRID 1668583 reaction equation
[C:1]([NH:4][C:5]1[CH:22]=[CH:21][C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13][C:7]=2[CH:6]=1)(=[S:3])[CH3:2].[OH-].[Na+]>CO.O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH3:2][C:1]1[S:3][C:22]2[C:5]([N:4]=1)=[CH:6][C:7]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:10][CH2:9][C:8]=1[CH:21]=2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59150495HCID 59150495, compound

Product 1

HCID 59150481HCID 59150481, compound

Reagents, catalysts & solvents 3

HCID 178511488HCID 178511488, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

1,1-dimethylethyl 7-(ethanethioylamino)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (411 mg), was dissolved in MeOH (12 ml), and 1N NaOH (6.1 ml) and added to potassium ferricyanide [K3Fe(CN)6] (2.1 g), in H2O (12 ml). This mixture was warmed up to 60° C. for 1.5 h, cooled at rt. concentrated and the material thus obtained was purified by flash chromatography over silica gel, eluting with 20% ethyl acetate in hexane, affording a 2:1 mixture of title compound and its regioisomer (167 mg) that was further used as such.

Workup

  1. temperaturecooled at rt
  2. concentrationconcentrated
  3. customthe material thus obtained
  4. customwas purified by flash chromatography over silica gel
  5. washeluting with 20% ethyl acetate in hexane
  6. customaffording

Sources & evidence

ORD record
ord-4b0ce1b6eea647f5b4b8966a5e28ad28
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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