Oxalyl chloride → N-(1-methyl-1H-pyrazol-3-yl)-3,5-bis[(phenylmethyl)oxy]benzamide

HRID 548713Notes

Reaction equation

HRID 548713 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=1)[C:18](O)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:32][N:33]1[CH:37]=[CH:36][C:35]([NH2:38])=[N:34]1>C(Cl)Cl>[CH3:32][N:33]1[CH:37]=[CH:36][C:35]([NH:38][C:18](=[O:19])[C:17]2[CH:16]=[C:15]([O:14][CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:23]=[C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:21]=2)=[N:34]1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 993073,5-Bis(phenylmethoxy)benzoic acidHCID 1372541-Methyl-3-aminopyrazole

Product 1

HCID 53629651N-(1-methyl-1H-pyrazol-3-yl)-3,5-bis[(phenylmethyl)oxy]benzamideYield 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (7.71 mL, 89.7 mmol) was added dropwise to a suspension of 3,5-dibenzyloxybenzoic acid (20.0 g, 59.8 mmol) in DCM (0.5 L) under argon. The reaction was stirred at RT for 6 hours after which time the volatiles were removed in vacuo. The residue was taken up in DCM (300 mL) and a solution of 1-methyl-1H-pyrazol-3-amine (5.81 g, 59.8 mmol) in DCM (50 mL) was added dropwise. The resulting solution was stirred for 16 hours at RT after which time a precipitate had formed. The solid was isolated by filtration and recrystallised from ethanol to give the title compound as a white solid (14.8 g). 1H NMR δ (d6-DMSO): 3.84 (3H, s), 5.17 (4H, s), 6.59 (1H, d), 6.84 (1H, t), 7.33-7.46 (12H, m), 7.62 (1H, d), 10.83 (1H, s); m/z 414 (M+H)+.

Workup

  1. customwere removed in vacuo
  2. stirringThe resulting solution was stirred for 16 hours at RT after which time a precipitate
  3. customhad formed
  4. customThe solid was isolated by filtration
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-998c54efe3cb48a6a8ba31cecaed4b51
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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