Butanethiol → HCID 135621434, compound

HRID 1084830Notes

Reaction equation

HRID 1084830 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCC.C[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[N:19]=2)=[CH:14][CH:13]=1>ClCCl>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)[N:19]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8012ButanethiolHCID 6451240Aluminum(III) ChlorideHCID 14796247HCID 14796247, compound

Product 1

HCID 135621434HCID 135621434, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 250 ml of dichloromethane was suspended 22.4 g of anhydrous aluminium chloride. While stirring, 22.4 ml of butylmercaptan was added. After the mixture was stirred at room temperature for 1 hour, 17.7 g of 3-(4-methoxyphenyl)-1(4-methylphenyl)-1H-pyrazolo[3,4-b]pyridine was added thereto under ice-cooling. After the mixture was stirred at room temperature for 4 hours, the reaction mixture was poured into about 1 l of ice-water. The resulting crystals were collected by filtration, washed with water and recrystallized from methanol to give 13.8 g of 3-(4-hydroxyphenyl)-1-(4-methyl- phenyl)-1H-pyrazolo[3,4-b]pyridine, m.p. 201°-203° C.

Workup

  1. stirringAfter the mixture was stirred at room temperature for 1 hour
  2. temperatureunder ice-cooling
  3. stirringAfter the mixture was stirred at room temperature for 4 hours
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-718fe1ce1a1746b78c6ebc4d36a73bed
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

Loading…