Sodium Hydroxide → (6-Dipropylamino-1,5,6,7-tetrahydro-1-aza-s-indacen-3-yl)-phenyl methanone

HRID 1683892Notes

Reaction equation

HRID 1683892 reaction equation
[CH2:1]([N:4]([CH2:17][CH2:18][CH3:19])[CH:5]1[CH2:16][C:15]2[CH:14]=[C:13]3[C:9]([CH:10]=[CH:11][NH:12]3)=[CH:8][C:7]=2[CH2:6]1)[CH2:2][CH3:3].P(Cl)(Cl)(Cl)=O.[OH-:25].[Na+]>>[CH2:17]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:16][C:15]2[CH:14]=[C:13]3[C:9]([C:10]([C:6]([C:7]4[CH:8]=[CH:9][CH:13]=[CH:14][CH:15]=4)=[O:25])=[CH:11][NH:12]3)=[CH:8][C:7]=2[CH2:6]1)[CH2:18][CH3:19]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 19041580Dipropyl-(1,5,6,7-tetrahydro-1-aza-s-indacen-6-yl)amine

Product 1

HCID 70092660(6-Dipropylamino-1,5,6,7-tetrahydro-1-aza-s-indacen-3-yl)-phenyl methanoneYield 100%

Conditions

Temperature
85 °C

Procedure

A mixture of dipropyl-(1,5,6,7-tetrahydro-1-aza-s-indacen-6-yl)amine (31 mg, 0.12 mmol) N,N-dimethylbenzamide (36 mg, 0.24 mmol) and phosphorous oxychloride (14 μL, 23 mg, 0.15 mmol) was heated at 85° C. overnight. After cooling, 3M sodium hydroxide (4 mL) was added and the resulting mixture was heated at 85° C. for 1 hour. The mixture was cooled and extracted (ethyl acetate) three times. The organic solution was dried (magnesium sulfate), filtered and evaporated to yield 46 mg (100%) of the desired material.: MS m/z (relative intensity, 70 eV) 360 (M+, 12), 331 (100), 105 (38), 260 (31).

Workup

  1. temperatureAfter cooling
  2. temperaturethe resulting mixture was heated at 85° C. for 1 hour
  3. temperatureThe mixture was cooled
  4. extractionextracted (ethyl acetate) three times
  5. dry with materialThe organic solution was dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-52ac96ded74e494193298b44308bd4b5
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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