Hydrochloric Acid → HCID 178479590, compound

HRID 1277728Notes

Reaction equation

HRID 1277728 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH2:7][NH:8][S:9]([C:12]2[C:20]3[N:19]=[N:18][NH:17][C:16]=3[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[ClH:23].[N:24](OCCCCC)=O>C(O)C>[ClH:23].[NH:17]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([S:9]([NH:8][CH2:7][CH2:6][C:5]3[CH:21]=[CH:22][C:2]([NH:1][NH2:24])=[CH:3][CH:4]=3)(=[O:11])=[O:10])[C:20]=2[N:19]=[N:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10026Pentyl nitriteHCID 178507570HCID 178507570, compound

Product 1

HCID 178479590HCID 178479590, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-Aminophenethyl)benzotriazole-4-sulphonamide (4.53 g, 14 mM) was dissolved in a minimum of boiling ethanol (100 ml). The solution was cooled to -5°, saturated with dry hydrogen chloride and, after further cooling to -10°, amyl nitrite (1.84 g, 16 mM, 2.11 ml) was added over 10 minutes. The mixture was then stirred for 2 hours at -10°. The very small quantity of solid which remained was removed from the reaction mixture by filtration and the filtrate was added, all at once, to a solution of anhydrous stannous chloride (8.13 g, 43 mM) in ethanolic hydrogen chloride (10 ml) at 0°. The reaction mixture was stirred at 0° for 1 hour, left at 5° overnight and then poured into ether (1 liter). The solid which precipitated was collected (4.1 g).

Workup

  1. temperatureafter further cooling to -10°
  2. customThe very small quantity of solid which remained was removed from the reaction mixture by filtration
  3. additionthe filtrate was added
  4. customat 0°
  5. stirringThe reaction mixture was stirred at 0° for 1 hour
  6. waitleft at 5° overnight
  7. additionpoured into ether (1 liter)
  8. customThe solid which precipitated
  9. customwas collected (4.1 g)

Sources & evidence

ORD record
ord-1f1ea63eeb7d48c8b719f5a9cab04fd1
Source dataset
uspto-grants-1981_07
Patent number
US04278748

Reaction notes

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