Acetic Acid → (4-Bromo-2-propylphenyl)cyanamide

HRID 1993962Notes

Reaction equation

HRID 1993962 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]#[N:12])[CH2:2][CH3:3].C([O-])(=O)C.[Na+].C(O)(=O)C.[Br:22]Br>ClCCl.[Cl-].[Na+].O>[Br:22][C:8]1[CH:7]=[CH:6][C:5]([NH:10][C:11]#[N:12])=[C:4]([CH2:1][CH2:2][CH3:3])[CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 19012709(2-Propylphenyl)cyanamide

Product 1

HCID 71423727(4-Bromo-2-propylphenyl)cyanamideYield 24.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(2-propylphenyl)cyanamide (0.550 g, 3.43 mmol), sodium acetate (0.278 g, 3.4 mmol), and catalytic acetic acid were combined in dichloromethane (25 mL). Bromine (0.17 mL, 3.43 mmol) was added dropwise and allowed to stir 2.5 hours. The mixture was then poured into brine and extracted with diethylether. The solvent was dried over magnesium sulfate and evaporated in vacuo. The solid was triturated with 9/1 Hexane/acetone, filtered, and dried to give 4-bromo2-propylphenylcyanamide (0.200 g, 24%) an off white solid. HRMS: calcd for C10H11BrN2+H+, 239.01783; found (ESI-FTMS, [M+H]+), 239.01782.

Workup

  1. extractionextracted with diethylether
  2. dry with materialThe solvent was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe solid was triturated with 9/1 Hexane/acetone
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-94552077275d41d89d4a79919b5e3509
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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