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

HRID 1786173
Notes
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Reaction equation

HRID 1786173 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1363478709-Chloro-2-methoxymethyl-6H-1,3,3a,6-tetraaza-benzo[e]azulen-5-one

Product 1

HCID 684057249-Chloro-2-methoxymethyl-5-[1,2,4]triazol-1-yl-4H-1,3,3a,6-tetraaza-benzoazuleneYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

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

  1. additionwas added dropwise
  2. temperaturewas heated
  3. temperatureto reflux for 20 h
  4. temperatureAfter cooling to ambient temperature
  5. stirringstirring
  6. waitwas continued for another 30 min
  7. filtrationThe solid was filtered off
  8. washwashed with water (300 mL) and diethylether (200 mL)
  9. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes