Dimethyl-p-toluidine → HCID 22713506, compound

HRID 351847Notes

Reaction equation

HRID 351847 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[N:10]=[CH:11][N:12]4[C:18]=3[CH2:17][NH:16][C:15](=O)[C:14]3[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:13]4=3)[O:6][N:5]=2)[CH2:3][CH2:2]1.CN(C)C1C=CC(C)=CC=1.P(Cl)(Cl)([Cl:37])=O>ClC1C=CC=CC=1>[Cl:37][C:15]1[C:14]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:13]=2[N:12]2[C:18]([CH2:17][N:16]=1)=[C:9]([C:7]1[O:6][N:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[N:8]=1)[N:10]=[CH:11]2

Participants

5

Reactant 3

HCID 7471Dimethyl-p-toluidineHCID 24813Phosphorus oxychlorideHCID 227134693(-3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-8-bromo-4,5-dihydro-2,5,10b-triaza-benzo[e]azulene-6-one

Product 1

HCID 22713506HCID 22713506, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

3(-3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-8-bromo-4,5-dihydro-2,5,10b-triaza-benzo[e]azulene-6-one (1.1 g, 20.3 mmol) and N,N-dimethyl-p-toluidine (881 μL, 6.1 mmol) were mixed in chlorobenzene (8 mL) under Argon. Phosphorus oxychloride (279 μL, 3.1 mmol) was then added at room temperature and the resulting mixture heated under reflux for 2.5 h. After cooling, the mixture was evaporated and then extracted with CH2Cl2 (50 mL) and water (25 mL). The organic layer was separated, dried (Na2SO4) and evaporated. Chromatography on silica gel eluting with CH2Cl2: Acetone (30:1). Yield: 550 mg (67%). m/z 403/405 (M—H−).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 2.5 h
  3. temperatureAfter cooling
  4. customthe mixture was evaporated
  5. extractionextracted with CH2Cl2 (50 mL) and water (25 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-cf509b8f9531440cbfd930e6fe4559ef
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

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