Methyl iodide → HCID 80489592, compound

HRID 1486562Notes

Reaction equation

HRID 1486562 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]=[C:9]=[S:10])[CH:5]=[C:4]([Cl:11])[CH:3]=1.[C:12]([NH-:14])#[N:13].[Na+].[CH3:16]I>C(#N)C.CO>[C:12]([NH:14][C:9](=[N:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([Cl:11])[CH:5]=1)[S:10][CH3:16])#[N:13]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 1387763,5-Dichlorophenyl isothiocyanateHCID 4293993Sodium cyanamide

Product 1

HCID 80489592HCID 80489592, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,3-dichloro-5-isothiocyanatobenzene (10 g, 49.0 mmol, Adrich) in acetonitrile (90 ml) and MeOH (100 ml) was added a suspension of sodium hydrogencyanamide (3.45 g, 53.9 mmol) in MeOH (30 ml). The reaction was stirred at room temperature for 1 hour and methyl iodide (13.9 g, 6.13 ml, 98.0 mmol) was added. Continued stirring for 4 hours, and the reaction mixture was filtered, and washed with acetonitrile to give a white solid as desired product (8.04 g, 63% yield).

Workup

  1. stirringContinued stirring for 4 hours
  2. filtrationthe reaction mixture was filtered
  3. washwashed with acetonitrile

Sources & evidence

ORD record
ord-39e48a7eceb64e3ea273d803f95cb152
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

Loading…