Water → HCID 178519554, compound

HRID 591795Notes

Reaction equation

HRID 591795 reaction equation
[NH:1]1[C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=2)=[N:4][N:3]=[N:2]1.O>CS(C)=O>[NH:4]1[C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][CH:8]=2)=[N:1][N:2]=[N:3]1

Participants

4

Reactant 2

HCID 962WaterHCID 178519555HCID 178519555, compound

Product 1

HCID 178519554HCID 178519554, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

IBX (0.437 g, 1.562 mmol) was dissolved in anhydrous DMSO (5 mL) and [4-(1H-tetrazol-5-ylmethyl)-phenyl]-methanol (0.270 g, 1.562 mmol) was added. The reaction mixture was stirred at room temperature under nitrogen for 4 hours. Water (20 mL) was added. The white precipitate was filtered off, washed with water, and dried under vacuum. The crude compound was mixed with methanol (20 mL) and stirred for 30 minutes, before being filtered. The filtrate was concentrated to give 4-(1H-tetrazol-5-ylmethyl)-benzaldehyde as a white solid. Yield: 0.267 g (99%). To a solution of 2-amino-4,6-dimethoxybenzamide (0.157 g, 0.8 mmol) in N,N-dimethyl acetamide (5 mL) were added 4-(1H-tetrazol-5-ylmethyl)-benzaldehyde (0.260 g, 1.4 mmol), sodium hydrogen sulfite (58.5%, 0.159 g, 0.88 mmol) and p-toluenesulfonic acid (19 mg, 0.08 mmol). The reaction mixture was stirred at 150° C. for 3 h, then cooled to room temperature. Water (40 mL) was then added. A yellow precipitate was formed and filtered off, washed with water, and small amount of methanol. It was triturated with 10% methanol in ether to give 0.107 g of solid, which was further purified by preparative HPLC, to give the title compound (0.082 g, 28%) as a white solid. MS (ES) m/z: 365.1 (M+1). MP 295-296° C.

Workup

  1. filtrationThe white precipitate was filtered off
  2. washwashed with water
  3. customdried under vacuum
  4. additionThe crude compound was mixed with methanol (20 mL)
  5. stirringstirred for 30 minutes
  6. filtrationbefore being filtered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5757b45a66ab474399e0ead362a885de
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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