Dimethyl-p-toluidine → 6,8-Dichloro-3-(5-cyclopropyl-[1,2,4]oxadiazol-3-yl)-4H-2,5,10b-triaza-benzo[e]azulene

HRID 351853

Reaction equation

HRID 351853 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]3[C:10]([CH2:11][NH:12][C:13](=O)[C:4]=2[CH:3]=1)=[C:9]([C:15]1[N:19]=[C:18]([CH:20]2[CH2:22][CH2:21]2)[O:17][N:16]=1)[N:8]=[CH:7]3.CN(C)C1C=CC(C)=CC=1.P(Cl)(Cl)([Cl:37])=O>ClC1C=CC=CC=1>[Cl:37][C:13]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:24]=[CH:23][C:5]=2[N:6]2[C:10]([CH2:11][N:12]=1)=[C:9]([C:15]1[N:19]=[C:18]([CH:20]3[CH2:22][CH2:21]3)[O:17][N:16]=1)[N:8]=[CH:7]2

Participants

5

Reactant 3

HCID 7471Dimethyl-p-toluidineHCID 24813Phosphorus oxychlorideHCID 22713497HCID 22713497, compound

Product 1

HCID 227135456,8-Dichloro-3-(5-cyclopropyl-[1,2,4]oxadiazol-3-yl)-4H-2,5,10b-triaza-benzo[e]azuleneYield 63%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

8-Chloro-3-(5-cyclopropyl-[1,2,4]oxadiazol-3-yl)-4,5-dihydro-2,5,10b-triaza-benzo[e]azulen-6-one (0.84 g, 2.5 mmol) was suspended in chlorobenzene (8 mL), N,N-dimethyl-p-toluidine (1.1 mL, 7.4 mmol) and phosphorus oxychloride (0.34 mL, 3.7 mmol) were added and the mixture was refluxed overnight. The resulting solution was evaporated and the residue was purified by chromatography on silica gel in CH2Cl2/acetone 10:1. One obtained a white solid (0.56 g, 63%). mp 200° C. m/z 359(M).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe resulting solution was evaporated
  3. customthe residue was purified by chromatography on silica gel in CH2Cl2/acetone 10:1

Sources & evidence

ORD record
ord-80f739d1ea654a9eb6c80e6283701e33
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Linked notes

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