Cyanamide → HCID 86711621, compound

HRID 527351Notes

Reaction equation

HRID 527351 reaction equation
[N:1]#[C:2][NH2:3].CC(C)([O-])C.[K+].[F:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=1[S:29][CH3:30])[CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25].BrN1C(=O)CCC1=O>CO>[F:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=1[S:29]([CH3:30])=[N:1][C:2]#[N:3])[CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25]

Participants

6

Reactant 4

HCID 9864CyanamideHCID 67184N-bromobutanimideHCID 23665647Potassium tert-butoxideHCID 86711601HCID 86711601, compound

Product 1

HCID 86711621HCID 86711621, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyanamide (350 mg, 8.20 mmol) and potassium tert-butoxide (860 mg, 7.60 mmol) are added to a solution of 2-(3-fluoro-4-methylsulfanyl-benzyl)-isoindole-1,3-dione (preparation 15a, 2.00 g, 6.31 mmol) in methanol (50 mL). N-Bromosuccinimide (1.70 g, 9.50 mmol) is added and the mixture is stirred at room temperature over night. All volatiles are removed under reduced pressure, and the residue is treated with dichloromethane (20 mL). The mixture is washed with saturated aqueous sodium chloride solution, dried over Na2SO4 and concentrated under reduced pressure. The residue is directly used in the next step without further purification. Yield: 1.61 g (60% of theory); ESI mass spectrum: [M+H]+=342; r.t. HPLC: 0.76 min (5-95AB).

Workup

  1. customAll volatiles are removed under reduced pressure
  2. additionthe residue is treated with dichloromethane (20 mL)
  3. washThe mixture is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is directly used in the next step without further purification
  7. customr.t
  8. custom0.76 min (5-95AB)

Sources & evidence

ORD record
ord-35e055ed3d76434fbf92091004c6f97e
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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