Hydrochloric Acid → 2-Methyl-5-pyrazin-2-yl-2h-[1,2,4]triazole-3-carbaldehyde dihydrochloride monohydrate

HRID 859705Notes

Reaction equation

C([O:3][CH:4](OCC)[C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]2[CH:16]=[N:15][CH:14]=[CH:13][N:12]=2)[N:6]=1)C.[ClH:20]>O>[OH2:3].[ClH:20].[ClH:20].[CH3:10][N:9]1[C:5]([CH:4]=[O:3])=[N:6][C:7]([C:11]2[CH:16]=[N:15][CH:14]=[CH:13][N:12]=2)=[N:8]1

Participants

Conditions

Temperature: 60 °C

Procedure

The acetal from step 2, 2-[5-(diethoxymethyl)-1-methyl-1H-1,2,4-triazol-3-yl]pyrazine (44.5 g, 0.17 mol) was dissolved in water (150 mL) and conc. HCl (30.0 mL of 12 M, 0.36 mol, ˜2 equiv). The solution was degassed with nitrogen for 2 min and heated in an oil bath at a bath temperature of 60° C for 2 h, resulting in complete hydrolysis of the acetal group. The volatiles were removed in vacuo, affording a yellow solid (49.8 g). This was suspended in dichloromethane (1 L), refluxed under nitrogen for 1 h, then filtered while still hot. The filter cake was washed with dichloromethane and dried in vacuo at 50° C. for 4 h, affording the title product (41.0 g, 81%) as a hygroscopic yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 4.21 (s, 3H), 8.50 (br s, 4H), 8.75 (m, 2H), 9.27 (s, 1H), 10.01 (s, 1H). MS (APCI) calcd for C8H7N5O: 189.07, found (M+H+): 190.1, 208.1 (hydrate); Anal. Calcd. For C8H11Cl2N5O2: C, 34.30; H, 3.96; N, 25.00; O, 11.42; Cl, 25.31. Found: C, 33.43; H, 3.98; N, 24.70; O, 11.17; Cl, 25.44.

Workup

customThe solution was degassed with nitrogen for 2 min
customresulting in complete hydrolysis of the acetal group
customThe volatiles were removed in vacuo

Sources & evidence

ORD record: ord-d8526171df474414a2e81e24d07d10d1
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151105B2

Reaction notes

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