Dimethylformamide → 3-{2-[(4-Methoxyphenyl)methyl]-2H-tetrazol-5-yl}benzoyl chloride

HRID 349444Notes

Reaction equation

HRID 349444 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16](O)=[O:17])=[N:9]2)=[CH:5][CH:4]=1.C(Cl)(=O)C([Cl:27])=O.CN(C=O)C>ClCCl>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([Cl:27])=[O:17])=[N:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 68979330HCID 68979330, compound

Product 1

HCID 713752243-{2-[(4-Methoxyphenyl)methyl]-2H-tetrazol-5-yl}benzoyl chlorideYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The carboxylic acid intermediate (10 g, 0.032 mol) from Step (c) was suspended in dichloromethane followed by the addition of oxalyl chloride (20.4 g, 0.16 mol) and catalytic DMF. The reaction mixture was stirred at room temperature for 3 hours, at which time dissolution was nearly complete. The reaction mixture was filtered and concentrated in vacuo. The residue was triturated with petroleum ether and collected by filtration to give the title compound (9.5 g, 90%) as a white solid. 1H NMR (CDCl3) δ 8.9 (s, 1H), 8.5 (d, 1H), 8.2 (d, 1H), 8.6 (t, 1H), 7.4 (d, 2H), 6.9 (d, 2H), 3.8 (s, 3H) ppm. Mp 122–124° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with petroleum ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1f0e68d1fd964cdc964c6b55a681223a
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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