Sulfuric Acid → HCID 23462867, compound

HRID 2286396Notes

Reaction equation

HRID 2286396 reaction equation
S(=O)(=O)(O)O.N[C:7]1[C:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C:11]=2[C:10]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:9][CH:8]=1.N([O-])=[O:27].[Na+].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.[OH-].[NH4+]>O>[OH:27][C:7]1[C:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C:11]=2[C:10]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 23462873HCID 23462873, compoundHCID 23668193Sodium NitriteHCID 54670067L-Ascorbic Acid

Product 1

HCID 23462867HCID 23462867, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a stirred solution of 114 ml. of water and 15 ml. of concentrated sulfuric acid at 60°-70° C. is added 23.2 g. (0.082 mole) of 9-amino-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine. The resulting suspension is stirred vigorously and cooled to 0°-5° C. To this suspension is added 6.3 g. (0.091 mole) of sodium nitrite in 10 ml. of water at a rate such that the temperature does not exceed 5° C. The resulting diazonium solution is added dropwise to a boiling solution of 200 g. of cuprous sulfate and 300 ml. of water. After being refluxed for 15 minutes the solution is cooled, a trace of ascorbic acid is added and the pH is adjusted to 7.0 with ammonium hydroxide. The mixture is extracted with ethyl acetate. After being dried the extract is concentrated to afford 9-hydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine. Purification is accomplished by chromatography or by recrystallization of an appropriate acid addition salt.

Workup

  1. temperaturecooled to 0°-5° C
  2. additionTo this suspension is added 6.3 g
  3. customdoes not exceed 5° C
  4. temperatureAfter being refluxed for 15 minutes the solution
  5. temperatureis cooled
  6. extractionThe mixture is extracted with ethyl acetate
  7. customAfter being dried the extract
  8. concentrationis concentrated

Sources & evidence

ORD record
ord-661cd59f7d0b4b9f9fb1cfb90dc3ff04
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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