Water → HCID 16065919, compound

HRID 240314

Reaction equation

HRID 240314 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.BrN1C(=O)CCC1=O.O.[NH2:21]/[C:22](/[C:27]#[N:28])=[C:23](\[NH2:26])/[C:24]#[N:25]>CS(C)=O.CC(O)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[C:7](=[O:11])[C:6]3[C:5]([C:4]=2[CH:3]=1)=[N:21][C:22]([C:27]#[N:28])=[C:23]([C:24]#[N:25])[N:26]=3

Participants

7

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 1425995-Chloro-1-indanoneHCID 2723951Diaminomaleonitrile

Product 1

HCID 16065919HCID 16065919, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-chloro-1-indanone (1.05 g, 6.28 mmol) and N-bromosuccinimide (2.23 g, 12.56 mmol) in DMSO (25 ml) was stirred overnight at 40° C. and 5 h at 80° C. under vacuum. Water (125 ml) was added and the mixture was extracted with CH2Cl2 (25 ml). The aqueous phase was saturated with brine and solid NaCl and extracted with CH2Cl2 (4×80 ml). The collected organic phases were dried over Na2SO4 and the solvent evaporated. The crude was dissolved in EtOH (63 ml), diaminomaleonitrile (678 mg, 6.28 mmol) and a catalytic amount of AcOH were added and the mixture stirred at 80° C. for 45 min. The precipitate was collected by filtration and washed with EtOH (464 mg). The filtered solution was evaporated and the crude purified by flash.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (25 ml)
  2. extractionextracted with CH2Cl2 (4×80 ml)
  3. dry with materialThe collected organic phases were dried over Na2SO4
  4. customthe solvent evaporated
  5. dissolutionThe crude was dissolved in EtOH (63 ml)
  6. stirringthe mixture stirred at 80° C. for 45 min
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with EtOH (464 mg)
  9. customThe filtered solution was evaporated
  10. customthe crude purified by flash

Sources & evidence

ORD record
ord-277339e11b364d9fb2cd6bac8bd778bc
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Linked notes

Loading…