Ethanol → HCID 19817095, compound

HRID 1087498Notes

Reaction equation

HRID 1087498 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[C:27]5[CH:28]=[CH:29][CH:30]=[C:21]([C:22]=45)[S:20]3(=[O:32])=[O:31])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C(O)C.[BH4-].[Na+].[OH-].[Na+]>O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[C:27]5[CH:28]=[CH:29][CH:30]=[C:21]([C:22]=45)[S:20]3(=[O:32])=[O:31])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 15710733HCID 15710733, compound

Product 1

HCID 19817095HCID 19817095, compoundYield 8.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-{3-[4-(4-Nitrophenyl)-1-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (30 g), stannous chloride dihydrate (74.8 g) and ethanol (500 cc) are heated for one hour at 60° C. under a current of argon. Then sodium borohydride (1.3 g) is added over one hour in small portions. Stirring is continued for one hour at 60° C., then for 15 hours at a temperature of about 20° C. The mixture is poured into water and ice (500 cc) then alkalinized with 4N caustic soda to pH 9. The organic phase is extracted with diethyl ether (4×200 cc), absorbed in charcoal 3S (3 g), dried on anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (200 mm Hg; 2.7 kPa). The residue obtained in purified by recrystallization, first from boiling 1-propanol (250 cc), then twice from boiling ethanol (20 cc). 2-{3 -[4-(4-Aminophenyl)-1-piperazinyl] propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (2.4 g) is thus obtained, m.p. 113° C.

Workup

  1. waitfor 15 hours at a temperature of about 20° C
  2. extractionThe organic phase is extracted with diethyl ether (4×200 cc)
  3. customabsorbed in charcoal 3S (3 g)
  4. dry with materialdried on anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (200 mm Hg; 2.7 kPa)
  7. customThe residue obtained
  8. customin purified by recrystallization

Sources & evidence

ORD record
ord-eab6ca0f35aa4c6c87948065e0a1e1cf
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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