Butanethiol → HCID 135667574, compound

HRID 234051Notes

Reaction equation

HRID 234051 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCC.[CH2:10]([C:12]1[S:21][C:20]2[N:19]3[C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[N:23][N:24]=[C:18]3[CH2:17][N:16]=[C:15]([C:36]3[CH:41]=[CH:40][C:39]([O:42]C)=[CH:38][CH:37]=3)[C:14]=2[CH:13]=1)[CH3:11]>ClCCl>[CH2:10]([C:12]1[S:21][C:20]2[N:19]3[C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[N:23][N:24]=[C:18]3[CH2:17][N:16]=[C:15]([C:36]3[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=3)[C:14]=2[CH:13]=1)[CH3:11]

Participants

5

Reactant 3

HCID 8012ButanethiolHCID 6451240Aluminum(III) ChlorideHCID 18917605HCID 18917605, compound

Product 1

HCID 135667574HCID 135667574, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous aluminum chloride (78.1 g) was suspended in dichloromethane (700 ml) and thereto was dropwise added n-butylmercaptan (106 ml) with stirring under ice-cooling. Thereto was added 2-ethyl-4-(4-methoxylphenyl)-9-undecyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (40 g) obtained in Example 1 under ice-cooling. After stirring at room temperature for 20 hours, the reaction mixture was washed with 5% aqueous sodium hydrogencarbonate and water and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to give 20 g of 2-ethyl-4-(4-hydroxyphenyl)-9-undecyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine as crystals, melting point 164.5°-166.5° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringAfter stirring at room temperature for 20 hours
  4. washthe reaction mixture was washed with 5% aqueous sodium hydrogencarbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-169ff725d767436dbe9f80aaca6ef1f3
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

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