Isopropanol → HCID 13077563, compound

HRID 542851Notes

Reaction equation

HRID 542851 reaction equation
Br.Br.Br.[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:15]=1)[N:12]=[CH:11][CH:10]=[C:9]2[CH3:29].CC(O)C.[OH-].[NH4+].[C:36]([N:38]=[C:39](SC)[S:40][CH3:41])#[N:37]>O.C1(C)C=CC=CC=1>[C:36]([N:38]=[C:39]([N:26]1[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:14]2[CH:15]=[C:6]([O:5][CH3:4])[CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[C:9]3[CH3:29])[CH2:28][CH2:27]1)[S:40][CH3:41])#[N:37]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 14923Ammonium HydroxideHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 131715103HCID 131715103, compound

Product 1

HCID 13077563HCID 13077563, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 5.5 g (0.009 mole) of 6-methoxy-4-methyl-N-[6-(1-piperazinyl)hexyl]-8-quinolinamine, trihydrobromide, compd. with 2-propanol (1:0.3), hemihydrate in 100 ml of water was made basic with concentrated ammonium hydroxide and extracted with dichloromethane. The extract was washed, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under vacuum. A solution of the concentrate and 1.8 g (0.012 mole) of cyanodithioimidocarbonic acid, dimethyl ester in 100 ml of toluene was stirred at room temperature for 64 hours, then washed with water, dried, and concentrated to dryness. Recrystallization from 2-propanol afforded 2.7 g (66%) of the title compound as yellow needles, mp 97°-99°.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under vacuum
  6. concentrationA solution of the concentrate
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated to dryness
  10. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-1c279f289bb44b3fabf2079bcb5080cf
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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