Hydrochloric Acid → HCID 23462877, compound

HRID 2286395Notes

Reaction equation

HRID 2286395 reaction equation
[ClH:1].Cl.N[C:4]1[C:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][C:8]=2[C:7]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1.Cl.N([O-])=O.[Na+]>O>[Cl:1][C:4]1[C:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][C:8]=2[C:7]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23462880HCID 23462880, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23462877HCID 23462877, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred suspension of 17.9 g. (0.05 mole) of 9-amino-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine dihydrochloride in 50 ml. of water and 50 ml. of concentrated hydrochloric acid at 0°-5° C. is added dropwise a solution of 4.2 g. (0.06 mole) of sodium nitrite in 25 ml. of water. After being stirred at 0°-5° C. for 30 minutes, the resulting diazonium solution is added to a solution of 6.0 g. (0.06 mole) of cuprous chloride in 25 ml. of concentrated hydrochloric acid. The mixture is stirred for 16 hours at 25° C., then it is warmed to 60°-80° C. for 1 hour. After being cooled to 15°-20° C., the mixture is made alkaline and extracted with ether. The ether extract is dried over magnesium sulfate and concentrated to leave 9-chloro-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine which is purified by chromatography or by recrystallization of appropriate acid addition salts; hydrochloride salt m.p. 231°-232° C.

Workup

  1. additionTo a stirred suspension of 17.9 g
  2. stirringThe mixture is stirred for 16 hours at 25° C.
  3. temperatureit is warmed to 60°-80° C. for 1 hour
  4. temperatureAfter being cooled to 15°-20° C.
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. dry with materialis dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-76d6996dfc2c439ebfc58c04a174f7cc
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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