Phenyl Isothiocyanate → HCID 18521791, compound

HRID 413730Notes

Reaction equation

HRID 413730 reaction equation
[Na].[N:2]#[C:3][NH2:4].[C:5]1([N:11]=[C:12]=[S:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1)=[O:17]>CO.O>[NH2:2][C:3]1[N:4]=[C:12]([NH:11][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[S:13][C:15]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1)=[O:17]

Participants

7

Reactant 4

HCID 7673Phenyl IsothiocyanateHCID 9864CyanamideHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 5360545Sodium

Product 1

HCID 18521791HCID 18521791, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Following the procedure of Gewald et al., J. Prakt. Chem., vol. 35 (1967), pp. 97-104, sodium (188 mg, 8.20 mmol) was carefully dissolved in methanol (9 mL) at 0° C. and allowed to warm to ambient temperature. The resultant solution was added portionwise to a mixture of cyanamide (345 mg, 8.20 mmol) and phenyl isothiocyanate (0.98 mL, 8.2 mmol), whereupon heat evolved. 2-Bromo-3′-nitroacetophenone (2.00 g, 8.2 mmol) was added, and the resultant mixture stirred overnight at ambient temperature. The mixture was diluted with water (150 mL). A yellow-brown solid was filtered off, rinsed with water and a small amount of ether, dried under vacuum, and recrystallized from ethanol to give 2.17 g (52% yield) of the title compound in the form of dark brown crystals, melting point (mp) 186-187° C.

Workup

  1. temperaturewhereupon heat
  2. filtrationA yellow-brown solid was filtered off
  3. washrinsed with water
  4. dry with materiala small amount of ether, dried under vacuum
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b184b47f63ae4f6c94669374fdab15fc
Source dataset
uspto-grants-2003_05
Patent number
US06569878B1

Reaction notes

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