Benzyl Isothiocyanate → N-Benzyl-N'-(3-chloro-5-trifluoromethyl-2-pyridyl)methylthiourea

HRID 2416014Notes

Reaction equation

HRID 2416014 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH2:13][NH2:14])=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:15]([N:22]=[C:23]=[S:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.C(N(CC)CC)C>[CH2:15]([NH:22][C:23]([NH:14][CH2:13][C:4]1[C:3]([Cl:2])=[CH:8][C:7]([C:9]([F:12])([F:10])[F:11])=[CH:6][N:5]=1)=[S:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 2346Benzyl IsothiocyanateHCID 114997441-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine--hydrogen chloride (1/1)

Product 1

HCID 22637232N-Benzyl-N'-(3-chloro-5-trifluoromethyl-2-pyridyl)methylthiourea

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (3-chloro-5-trifluoromethyl-2-pyridyl)methylamine hydrochloride (0.12 g) and benzylisothiocyanate (0.11 g) in dry tetrahydrofuran (10 ml) was added triethylamine (10 drops) and the mixture stirred at room temperature for 12 hours. The solvent was evaporated and ethyl acetate added. The mixture was washed with 2M hydrochloric acid and then with saturated sodium bicarbonate solution. The organic layer was separated and the solvent removed to give the title product. 1H N.M.R. δ(ppm) 4.7 (2H, broad s), 4.95 (2H, d), 6.9 (1H, broad s), 7.3-7.55 (6H, m), 7.95 (1H, s) and 8.58 (1H, s).

Workup

  1. customThe solvent was evaporated
  2. additionethyl acetate added
  3. washThe mixture was washed with 2M hydrochloric acid
  4. customThe organic layer was separated
  5. customthe solvent removed

Sources & evidence

ORD record
ord-28e0e1d6a64047fa93a0ce93b34299c0
Source dataset
uspto-grants-2004_11
Patent number
US06821992B1

Reaction notes

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