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

HRID 1666936Notes

Reaction equation

HRID 1666936 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(OCC)(=O)C.C(O)(C)C.[Pd]>[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

6

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 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
81 °C

Procedure

2-(2-Nitroanilino)-5-methylthiophene-3-carbonitrile (100 g) is taken in ethyl acetate (1000 ml). 5% Pd/C (15 g) is added and hydrogenated at 50° C. for 15 hours. Ethyl acetate is distilled off to get the solid. The solid is taken in isopropyl alcohol (500 ml), concentrated hydrochloric acid (102 ml) is added at room temperature and the mixture is heated up to 80-82° C. for 12 hours under stirring. The solution is cooled to precipitate the solid, filtered and dried under vacuum at 55-60° C. to give the title compound (80 g).

Workup

  1. distillationEthyl acetate is distilled off
  2. customto get the solid
  3. temperatureThe solution is cooled
  4. customto precipitate the solid
  5. filtrationfiltered
  6. customdried under vacuum at 55-60° C.

Sources & evidence

ORD record
ord-65c313b7c3e44b2c886ea789c11ccc82
Source dataset
uspto-grants-2011_10
Patent number
US08044196B2

Reaction notes

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