Thionyl Chloride → 7-[chloro(1-methyl-1H-imidazol-5-yl)(4-methylphenyl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a]quinazoline. hydrochloride

HRID 1788064Notes

Reaction equation

HRID 1788064 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:27]4[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=4)([C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)O)[CH:16]=3)[N:11]3[N:33]=[N:34][N:35]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:38])=O>>[ClH:1].[Cl:38][C:18]([C:27]1[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=1)([C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]1[N:33]=[N:34][N:35]=[C:10]1[N:9]=[C:8]2[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 686877095-(3-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanol

Product 1

HCID 1317273757-[chloro(1-methyl-1H-imidazol-5-yl)(4-methylphenyl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a]quinazoline. hydrochloride

Conditions

Temperature
60 °C

Procedure

A mixture of intermediate 25 (0.0083 mol) in thionyl chloride (80 ml) was stirred at 60° C. for 3 hours, then cooled and the solvent was evaporated. The residue was taken up in DCM. The solvent was evaporated, yielding 7-[chloro(1-methyl-1H-imidazol-5-yl)(4-methylphenyl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a]quinazoline. hydrochloride (1:1) (intermediate 26). This product was used directly in the next reaction step.

Workup

  1. temperaturecooled
  2. customthe solvent was evaporated
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d1bbf580442944608dde689b3a7fc372
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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