4-Toluenesulfonyl chloride → HCID 86758050, compound

HRID 1934585Notes

Reaction equation

HRID 1934585 reaction equation
[OH:1][CH:2]([CH3:31])[CH:3]([N:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH:7]=[N:6]1)[CH3:4].[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([N:20]2[CH2:19][CH2:18][N:17]([C:14]3[CH:13]=[CH:12][C:11]([N:8]4[CH:7]=[N:6][N:5]([CH:3]([CH3:4])[CH:2]([O:1][S:38]([C:35]5[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=5)(=[O:40])=[O:39])[CH3:31])[C:9]4=[O:10])=[CH:16][CH:15]=3)[CH2:22][CH2:21]2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 22743447HCID 22743447, compound

Product 1

HCID 86758050HCID 86758050, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of [S-(R*,S*)]-2,4-dihydro-2-(2-hydroxy-1-methylpropyl)4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (0.01 mol), p-toluene-sulfonyl chloride (0.012 mol), triethylamine (2 g) and dimethylaminopyridine (0.5 g) in CH2Cl2 (100 ml) was stirred at room temperature for 4 days. The mixture was taken up in CH2Cl2 and purified by column chromatography over silica gel (eluent: CH2Cl2 100%). The pure fractions were collected and the solvent was evaporated. The residue was triturated in methylisobutyl keton, filtered off and dried, yielding 4.6 g (79%) [S-(R*,S*)]-2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-[1-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]propyl]-3H-1,2,4-triazol-3-one (interm. 134).

Workup

  1. custompurified by column chromatography over silica gel (eluent: CH2Cl2 100%)
  2. customThe pure fractions were collected
  3. customthe solvent was evaporated
  4. customThe residue was triturated in methylisobutyl keton
  5. filtrationfiltered off
  6. customdried

Sources & evidence

ORD record
ord-6ed7c44caba14ee3ac41aeba60bd7987
Source dataset
uspto-grants-2002_05
Patent number
US06384030B1

Reaction notes

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