Hydrochloric Acid → 10H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

HRID 613243

Reaction equation

HRID 613243 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[NH:6][C:7]1[S:8][C:9]([CH3:14])=[CH:10][C:11]=1[C:12]#[N:13])([O-])=O.[ClH:19]>C(O)C>[ClH:19].[NH2:13][C:12]1[C:11]2[CH:10]=[C:9]([CH3:14])[S:8][C:7]=2[NH:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:1]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3954605-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile

Product 1

HCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred slurry of 2-(2-nitroanilino)-5-methyl-thiophene-3-carbonitrile (3 g, 0.011 mol) in ethanol (35 mL) at 50° C. was added, over 10 minutes, a solution of anhydrous stannous chloride (6.95 g, 0.037 mol) in hydrochloric acid (26 mL, 5M). The mixture was stirred under reflux for 1 hour, concentrated under reduced pressure and allowed to crystallize over night at 5° C. The salt was filtered, washed with a small amount of water, dried (4.3 g) m.p. >250° C., and used without further purification in the next stage.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. customto crystallize over night at 5° C
  4. filtrationThe salt was filtered
  5. washwashed with a small amount of water
  6. customdried (4.3 g) m.p. >250° C.
  7. customused without further purification in the next stage

Sources & evidence

ORD record
ord-d716f2b059914058a5eab7ef04e28b78
Source dataset
uspto-grants-1999_12
Patent number
US06008216

Linked notes

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