1-Chloro-2-isothiocyanatobenzene → 1-((3-Chloro-5-(trifluoromethyl)pyridin-2-yl)methyl)-3-(2-chlorophenyl)thiourea

HRID 2416007Notes

Reaction equation

HRID 2416007 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.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]=[C:23]=[S:24]>O1CCCC1.C(N(CC)CC)C>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[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]

Participants

5

Reactant 2

HCID 1231711-Chloro-2-isothiocyanatobenzeneHCID 114997441-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine hydrochloride

Product 1

HCID 226372191-((3-Chloro-5-(trifluoromethyl)pyridin-2-yl)methyl)-3-(2-chlorophenyl)thiourea

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (3-chloro-5-trifluoromethyl-2-pyridyl)methylamine hydrochloride (0.12 g) and 2-chlorophenylisothiocyanate (0.09 g) in dry tetrahydrofuran (10 ml) was added 10 drops of triethylamine. The mixture was stirred at room temperature overnight. The solvent was removed by evaporation in vacuo and the residue extracted with ethyl acetate and washed with 2M hydrochloric acid. The layers were separated and the organic phase was evaporated to dryness to give the title product, m.p. 126° C.

Workup

  1. customThe solvent was removed by evaporation in vacuo
  2. extractionthe residue extracted with ethyl acetate
  3. washwashed with 2M hydrochloric acid
  4. customThe layers were separated
  5. customthe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-adcdd127e4904a5c8fbdc0437588f93d
Source dataset
uspto-grants-2004_11
Patent number
US06821992B1

Reaction notes

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