Acetic Acid → (+/-)-3-Methyl-spiro[imidazolidine-4,2'-indane]-2,5-dione

HRID 1623079Notes

Reaction equation

HRID 1623079 reaction equation
Cl.[CH3:2][NH:3][C:4]1([C:13]#[N:14])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1.[O-:15][C:16]#N.[K+].CC(O)=[O:21]>O>[CH3:2][N:3]1[C:4]2([CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5]2)[C:13](=[O:21])[NH:14][C:16]1=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 184403032-(Methylamino)indane-2-carbonitrile hydrochloride

Product 1

HCID 18440308(+/-)-3-Methyl-spiro[imidazolidine-4,2'-indane]-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 2-(methylamino)indane-2-carbonitrile hydrochloride from Step A (6.0 g, 28.8 mmol) in AcOH (45 mL) was added a solution of potassium cyanate (4.65 g, 57 mmol) in H2O (6 mL) and the reaction mixture was stirred for 1 h. The mixture was poured into cold H2O (150 mL) and the precipitate was isolated by filtration, washed with H2O and air dried. The crude solid was suspended in 1 N HCl (30 mL) and stirred to 50° C. for 2 h. The reaction mixture was cooled, filtered, and the isolated solid washed with H2O and dried in vacuo to yield the title compound. MS: m/z=217 (M+1).

Workup

  1. customthe precipitate was isolated by filtration
  2. washwashed with H2O and air
  3. customdried
  4. stirringstirred to 50° C. for 2 h
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. washthe isolated solid washed with H2O
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c86df04bb55b43b1b5fe28d6e7fbdc84
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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