Potassium tert-butoxide → HCID 68155891, compound

HRID 1877792Notes

Reaction equation

HRID 1877792 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]1[C:16]([O:18]CC)=O.CC(C)([O-])C.[K+]>CS(C)=O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:16](=[O:18])[C:11]3=[CH:12][C:13]([CH3:15])=[CH:14][N:10]3[CH2:9][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 68155862HCID 68155862, compound

Product 1

HCID 68155891HCID 68155891, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 1-[(2-amino-5-chloro-phenyl)methyl]-4-methyl-pyrrole-2-carboxylate (35 g, 119.55 mmoles) in dimethyl sulfoxide (120 mL) add potassium t-butoxide (14.76 g, 131.5 mmoles) over 10 minutes. Heat at 80° C. (oil-bath temperature) for 1 h. Allow to cool then pour onto water (400 mL). Collect the resulting brown powdery solid by filtration, washing well with water. Suck as dry as possible on the sinter then transfer to a dish and dry in a vacuum oven at 55° C. over phosphorus pentoxide overnight, to give 7-chloro-2-methyl-5,10-dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one (22 g, 91%). MS (m/z): 247.1 (M+1).

Workup

  1. temperatureto cool
  2. additionthen pour onto water (400 mL)
  3. customCollect the resulting brown powdery solid
  4. filtrationby filtration
  5. washwashing well with water
  6. customSuck as dry as possible on the sinter
  7. dry with materialdry in a vacuum oven at 55° C. over phosphorus pentoxide overnight

Sources & evidence

ORD record
ord-b35f43b6d9814d328bf7942d0d9dd0ad
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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