Cyanamide → HCID 23525769, compound

HRID 2415267Notes

Reaction equation

HRID 2415267 reaction equation
[N:1]#[C:2][NH2:3].CC(C)([O-])C.[K+].[C:10]([O:14][C:15]([N:17]1[CH2:20][CH:19]([O:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[S:30])=[CH:24][CH:23]=2)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)=[O:34]>C(#N)C.C(O)(C)(C)C.O>[C:10]([O:14][C:15]([N:17]1[CH2:20][CH:19]([O:21][C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:29]3[S:30][C:32]([C:33](=[O:34])[C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=4)=[C:2]([NH2:3])[N:1]=3)=[CH:26][CH:27]=2)[CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

8

Reactant 4

HCID 9864CyanamideHCID 27374513-Fluorophenacyl bromideHCID 23525774HCID 23525774, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23525769HCID 23525769, 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 19, 306 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 (TCl, 216 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, 480 mg, 99%. MS (ES) MH+=485.

Workup

  1. stirringAfter being stirred for 2 hours at room temperature
  2. extractionthe new mixture was extracted with ether
  3. dry with materialThe extract was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a24326752aea4e4aa3772697a57c8b59
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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