Cyanamide → HCID 60063784, compound

HRID 2415248Notes

Reaction equation

HRID 2415248 reaction equation
[N:1]#[C:2][NH2:3].CC(C)([O-])C.[K+].[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[S:32])=[CH:26][CH:25]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11].Br[CH2:34][C:35]([C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=1)=[O:36]>C(#N)C.C(O)(C)(C)C.O>[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]2[S:32][C:34]([C:35](=[O:36])[C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=3)=[C:2]([NH2:3])[N:1]=2)=[CH:26][CH:25]=1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

8

Reactant 4

HCID 9864CyanamideHCID 27374513-Fluorophenacyl bromideHCID 23665647Potassium tert-butoxideHCID 60063757HCID 60063757, compound

Product 1

HCID 60063784HCID 60063784, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

Cyanamide (46.2 mg, 1.1 mmol) was suspended in acetonitrile (5 mL). To the stirred suspension, potassium tert-butoxide (123 mg, 1.1 mmol) in 2 mL of tert-butanol was added followed by isothiocyanate (Example 1, 334 mg, 1 mmol). The mixture was stirred for 30 minutes at room temperature followed by the addition of 2-bromo-1-(3-fluoro-phenyl)-ethanone (TCI, 261 mg, 1 mmol). After being stirred for 2 hours at room temperature, the mixture was poured into water and the new mixture was extracted with ether. The extract was dried(Na2SO4) and concentrated to give the desired product as a yellow solid, 510 mg, 99%. MS (ES) MH+=513.

Workup

  1. stirringAfter being stirred for 2 hours at room temperature
  2. extractionthe new mixture was extracted with ether
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0e2a9dc9df77488c87f7fb281a9a446e
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

Loading…