Pyridine → 1-(4-methoxybenzyl)-1H-tetrazole-5-carbonyl chloride

HRID 325730Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12]([C:13]([O-])=[O:14])=[N:11][N:10]=[N:9]2)=[CH:5][CH:4]=1.[K+].N1C=CC=CC=1.C(Cl)(=O)C([Cl:28])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12]([C:13]([Cl:28])=[O:14])=[N:11][N:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 15 °C

Procedure

Potassium 1-(4-methoxybenzyl)-1H-tetrazole-5-carboxylate (10.0 g) and pyridine (1.8 ml) were stirred together in dry toluene (140 ml) at 10° C. Oxalyl chloride (30.7 ml) was added, and the mixture was stirred at 15° C. for 1 hour. The mixture was filtered and the residual solid was washed with dry toluene (100 ml). The filtrate and washings were combined and evaporated in vacuo to give crude 1-(4-methoxybenzyl)-1H-tetrazole-5-carbonyl chloride, which was used immediately in the next stage.

Workup

filtrationThe mixture was filtered
washthe residual solid was washed with dry toluene (100 ml)
customevaporated in vacuo

Sources & evidence

ORD record: ord-23f3d0619a874caf88e3a0f4f23674f1
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04442115

Reaction notes

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