Acetonitrile → N-acetyl-N-(6-chloro-3-pyridylmethyl)-S-methyl-N'-nitroisothiourea

HRID 1275366Notes

Reaction equation

HRID 1275366 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[N:13][N+:14]([O-:16])=[O:15])[S:11][CH3:12])=[CH:4][CH:3]=1.C(#N)C.[C:20](Cl)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([N:9]([CH2:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10](=[N:13][N+:14]([O-:16])=[O:15])[S:11][CH3:12])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6367Acetyl chlorideHCID 1361361971-(2-Chloro-5-pyridylmethyl)-2-methyl-3-nitroisothiourea

Product 1

HCID 86751713N-acetyl-N-(6-chloro-3-pyridylmethyl)-S-methyl-N'-nitroisothioureaYield 106%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of N-(6-chloro-3-pyridylmethyl)-S-methyl-N'-nitroisothiourea (1.3 g) and acetonitrile (10 ml) was added pyridine (1.6 g) and further dropwise acetyl chloride (0.79 g) under ice-cooling. After stirring for 1 hour under ice-cooling, the mixture was warmed to room temperature and stirred at the same temperature for 2 hours. The reaction mixture was concentrated and 50 ml of ether and 5 ml of 2N hydrochloric acid were added to the mixture which was then partitioned. The resultant organic layers were dried over anhydrous magnesium sulfate and concentrated to afford 1.6 g of N-acetyl-N-(6-chloro-3-pyridylmethyl)-S-methyl-N'-nitroisothiourea as a red oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred at the same temperature for 2 hours
  4. concentrationThe reaction mixture was concentrated
  5. addition50 ml of ether and 5 ml of 2N hydrochloric acid were added to the mixture which
  6. customwas then partitioned
  7. dry with materialThe resultant organic layers were dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-65ad15821a50496bb43af3ddf590908e
Source dataset
uspto-grants-2000_12
Patent number
US06160126

Reaction notes

Loading…