1H-1,2,4-Triazole → 9-Chloro-2-methoxymethyl-5-[1,2,4]triazol-1-yl-4H-1,3,3a,6-tetraaza-benzoazulene

HRID 1786173Notes

Reaction equation

[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(N(CC)C(C)C)(C)C.P(Cl)(Cl)(Cl)=O.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[NH:33][C:32](=O)[CH2:31][N:30]3[C:26](=[N:27][C:28]([CH2:35][O:36][CH3:37])=[N:29]3)[C:25]=2[CH:38]=1>C(#N)C.O>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[N:33]=[C:32]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)[CH2:31][N:30]3[C:26]([C:25]=2[CH:38]=1)=[N:27][C:28]([CH2:35][O:36][CH3:37])=[N:29]3

Participants

Conditions

Temperature: 2.5 °C

Procedure

1,2,4-Triazole (74.3 g, 1.08 mol) was dissolved in acetonitrile (850 mL) and N,N-diisopropylethylamine (195 mL, 1.14 mol) was added. After cooling to 0° C. phosphorous oxychloride (29.8 mL, 326 mmol) was added dropwise and the reaction mixture was stirred at 0-5° C. for 2 h. 9-Chloro-2-methoxymethyl-6H-1,3,3a,6-tetraaza-benzo[e]azulen-5-one (45.4 g, 279 mmol) was added at once and the resulting suspension was heated to reflux for 20 h. After cooling to ambient temperature, water (1.30 L) was added and stirring was continued for another 30 min. The solid was filtered off and washed with water (300 mL) and diethylether (200 mL). Drying in vacuo (65° C.) afforded the title compound (33.8 g, 63%) which was obtained as an off-white solid. MS: m/e=330.1 [M+H]+.

Workup

additionwas added dropwise
temperaturewas heated
temperatureto reflux for 20 h
temperatureAfter cooling to ambient temperature
stirringstirring
waitwas continued for another 30 min
filtrationThe solid was filtered off
washwashed with water (300 mL) and diethylether (200 mL)
customDrying in vacuo (65° C.)

Sources & evidence

ORD record: ord-2a4940bf20274760a754394e86f2677e
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507729B2

Reaction notes

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