Ethanol → HCID 23462873, compound

HRID 2286394Notes

Reaction equation

HRID 2286394 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][C:6]2[C:9]([N+:20]([O-])=O)=[CH:10][CH:11]=[C:12]([S:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]=2[CH2:4][CH2:3]1.C(O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:20][C:9]1[C:6]2[CH2:7][CH2:8][N:2]([CH3:1])[CH2:3][CH2:4][C:5]=2[C:12]([S:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium Dithionite2×HCID 23462870HCID 23462870, compound

Product 1

HCID 23462873HCID 23462873, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 15.7 g. (0.05 mole) of 3-methyl-9-nitro-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine in 350 ml. of ethanol and 125 ml. of water is added, in portions, 35 g. (0.2 mole) of sodium hydrosulfite. The mixture is stirred and refluxed for 16 hours, then an additional 52 g. (0.3 mole) of sodium hydrosulfite is added and refluxing is continued for 30 hours, allowing about one-half of the solvent to distill from the reaction during the last hour. The mixture is cooled, diluted with water, made alkaline with ammonium hydroxide and extracted with ethyl acetate. After being dried, the extract is concentrated to give 9-amino-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine which is purified by chromatography. A solution of the base in ethanol is treated with an excess of hydrogen chloride. Following addition of ether crystalline 9-amino-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine dihydrochloride is obtained.

Workup

  1. temperaturerefluxed for 16 hours
  2. temperaturerefluxing
  3. distillationto distill from the reaction during the last hour
  4. temperatureThe mixture is cooled
  5. additiondiluted with water
  6. extractionextracted with ethyl acetate
  7. customAfter being dried
  8. concentrationthe extract is concentrated

Sources & evidence

ORD record
ord-baf10e0eff624090b536879e2b3c8977
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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