Water → 5-(3-chlorophenyl)-7-[(4-chlorophenyl)[4-methyl-5-(methylthio)-4H-1,2,4triazol-3-yl]methyl]-tetrazolo[1,5-a]quinoline

HRID 346982Notes

Reaction equation

HRID 346982 reaction equation
IC.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]2[N:28]=[N:29][N:30]=[C:23]2[CH:22]=[C:21]3[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)[C:11]2[N:12]([CH3:17])[C:13]([SH:16])=[N:14][N:15]=2)=[CH:6][CH:5]=1.[CH3:38]O[Na].CO.O>CO>[Cl:37][C:33]1[CH:32]=[C:31]([C:21]2[C:20]3[C:25](=[CH:26][CH:27]=[C:18]([CH:10]([C:7]4[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=4)[C:11]4[N:12]([CH3:17])[C:13]([S:16][CH3:38])=[N:14][N:15]=4)[CH:19]=3)[N:24]3[N:28]=[N:29][N:30]=[C:23]3[CH:22]=2)[CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 178481698HCID 178481698, compoundHCID 178501943HCID 178501943, compound

Product 1

HCID 210820605-(3-chlorophenyl)-7-[(4-chlorophenyl)[4-methyl-5-(methylthio)-4H-1,2,4triazol-3-yl]methyl]-tetrazolo[1,5-a]quinolineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodomethane (0.0092 mol) was added to a mixture of intermediate (62) (0.0092 mol) and MeONa/MeOH (0.0092 mol) in methanol (50 ml). The mixture was stirred at room temperature overnight and poured out into water. The precipitate was filtered washed with diethyl ether and dried, yielding 4.8 g (98%) of 5-(3-chlorophenyl)-7-[(4-chlorophenyl)[4-methyl-5-(methylthio)-4H-1,2,4triazol-3-yl]methyl]-tetrazolo[1,5-a]quinoline, MS (ESI) m/z:532, 534, 536 (MH+) (intermediate 63).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-8b7f48731cc54ba780bc45248ce7b172
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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