Hydrochloric Acid → HCID 71815944, compound

HRID 532561Notes

Reaction equation

HRID 532561 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:21]4[CH2:22][C:23]5[S:24][CH:25]=[CH:26][C:27]=5[C:20]=4[N:19](COCC[Si](C)(C)C)[N:18]=3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.Cl>CO.[Fe]>[S:24]1[CH:25]=[CH:26][C:27]2[C:20]3[NH:19][N:18]=[C:17]([C:14]4[CH:13]=[CH:12][C:11]([NH:10][C:7]5[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=5)=[CH:16][CH:15]=4)[C:21]=3[CH2:22][C:23]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86699205HCID 86699205, compound

Product 1

HCID 71815944HCID 71815944, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

(4-Nitro-phenyl)-{4-[4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl]-phenyl}-amine (0.25 g, 0.5 mmol) was dissolved in MeOH and treated with concentrated HCl (0.16 mL, 5 mmol) and iron powder (0.34 g, 6.0 mmol). The reaction mixture was heated at 100° C. for 4 hr. The solution was cooled to room temperature and the resultant precipitate was filtered, washed with MeOH and concentrated under reduced pressure to provide the corresponding N-[4-(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-phenyl]-benzene-1,4-diamine (0.14 g, 0.4 mmol) as yellow solid in 80% yield.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with MeOH
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-34c5de41c136435e9423804567aaf2cf
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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