Water → HCID 22677751, compound

HRID 1837467Notes

Reaction equation

HRID 1837467 reaction equation
C(C1C=N[NH:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)(=O)C.[O-:15][C:16]#[N:17].[Na+].F[C:20](F)(F)[C:21]([OH:23])=O.O.[C:27](#[N:29])[CH3:28]>>[C:21]([N:29]1[CH2:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([C:16]([NH2:17])=[O:15])[CH2:28][CH2:27]1)(=[O:23])[CH3:20]

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 13809734HCID 13809734, compound

Product 1

HCID 22677751HCID 22677751, compound

Conditions

Temperature
50 °C

Procedure

To a solution of 4-acetylbenzodiazepine (20.0 g, 0.105 mole) in acetonitrile (100 ml) at room temperature was added sodium cyanate (27.4 g, 0.42 mole). The resulting suspension was heated to 50° C. and then trifluoroacetic acid (24.0 g, 0.21 mole) was added slowly dropwise over 30 min. Heating was continued at 50° C. for 1 h. The reaction mixture was cooled to room temperature and the solvent was evaporated to give a white residue. Water (160 ml) was added to the residue and the mixture was cooled in ice for 1 h. The solids were collected by filtration and washed with cold water. After drying under house vacuum 23.6 g (96% ) of product was obtained as a white solid.

Workup

  1. temperatureHeating
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was evaporated
  4. customto give a white residue
  5. temperaturethe mixture was cooled in ice for 1 h
  6. filtrationThe solids were collected by filtration
  7. washwashed with cold water
  8. dry with materialAfter drying under house vacuum 23.6 g (96% ) of product
  9. customwas obtained as a white solid

Sources & evidence

ORD record
ord-1a5435847bbd4b55ac850ab9a3fef3bc
Source dataset
uspto-grants-2004_08
Patent number
US06784172B2

Reaction notes

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