Sulfuric Acid → HCID 23462906, compound

HRID 2286397Notes

Reaction equation

HRID 2286397 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].N[C:10]1[CH:21]=[CH:20][C:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18][C:12]=2[C:11]=1[S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[S:29](=[O:33])(=[O:32])([OH:31])[OH:30].N([O-])=[O:35].[Na+].N(O)=O.NC(N)=O>>[S:29]([OH:33])([OH:32])(=[O:31])=[O:30].[OH:35][C:10]1[CH:21]=[CH:20][C:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18][C:12]=2[C:11]=1[S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 6

HCID 1118Sulfuric Acid2×HCID 1176UreaHCID 24489Sodium DithioniteHCID 24529Nitrous Acid2×HCID 23462883HCID 23462883, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23462906HCID 23462906, compound

Conditions

Temperature
0 °C

Procedure

Following the procedures outlined in Example 9, the isomeric 6-chloro-3-methyl-7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine is treated with sodium thiophenolate to give the 6-phenylthio intermediate and the nitro group is reduced with sodium hydrosulfite. To a solution of 2.6 g. (0.0125 mole) of the resulting 7-amino-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine in 25 ml. of 3 N sulfuric acid at 0°-3° C., a solution of sodium nitrite (1 g. in 5 ml. of water) is added dropwise until a positive test for nitrous acid is obtained. Excess nitrous acid is decomposed by adding 0.2 to 0.3 g. of urea and stirring for 10 minutes. The diazonium solution is added dropwise with stirring to 200 ml. of 50% sulfuric acid at 70° C. and maintained at 70° C. until all of the diazonium salt is decomposed. On cooling the warm solution in an ice bath a crystalline precipitate is formed. After being chilled for 30 minutes at 0° C., the mixture is filtered. The solid is washed with a small volume of ice/water. Recrystallization affords 7-hydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine sulfate.

Workup

  1. customis obtained
  2. additionby adding 0.2 to 0.3 g
  3. temperatureOn cooling the warm solution in an ice bath a crystalline precipitate
  4. customis formed
  5. filtrationthe mixture is filtered
  6. washThe solid is washed with a small volume of ice/water
  7. customRecrystallization

Sources & evidence

ORD record
ord-1f93d91603b04a1bb551bf013f7f7632
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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