Sodium Bisulfate → 1-{3-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}propyl)oxy]phenyl}methanamine

HRID 606443Notes

Reaction equation

HRID 606443 reaction equation
[C:1]1([C:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH:12]=[N:11][C:10]([S:13][CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])(O)(=O)=O.[Na+]>C1COCC1>[C:32]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:8]2[CH:12]=[N:11][C:10]([S:13][CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:19]=[C:20]([CH2:21][NH2:22])[CH:23]=[CH:24][CH:25]=3)=[N:9]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 667691893-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}propyl)oxy]benzonitrile

Product 1

HCID 667684731-{3-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}propyl)oxy]phenyl}methanamineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}propyl)oxy]benzonitrile obtained in Reference Example 6 (2.00 g, 3.98 mmol) in THF (15 mL) was added slowly to a suspension of lithium aluminum hydride (1.51 g, 39.8 mmol) in THF (45 mL) at room temperature, and the mixture was stirred at room temperature for 4 hr. Sodium hydrogensulfate 10 hydrate (5.13 g, 15.9 mmol) was added to the reaction mixture at 0° C., and mixture was stirred at room temperature for 30 min. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Toluene and ethanol were added to the residue, and the mixture was concentrated under reduced pressure to give the title compound as a pale-yellow oil (1.91 g, 95%).

Workup

  1. stirringmixture was stirred at room temperature for 30 min
  2. filtrationThe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionToluene and ethanol were added to the residue
  5. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b23f3f4eafa8461d84fc515a24edc789
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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