1,3-Dichloro-2-isothiocyanatobenzene → HCID 86664891, compound

HRID 2368659Notes

Reaction equation

HRID 2368659 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[C:5]([NH:10][CH3:11])=[N:6][C:7]=1[O:8][CH3:9].[H][H].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[N:25]=[C:26]=[S:27]>C1COCC1.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]([NH:12][C:26]([NH:25][C:19]2[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:18]=2[Cl:17])=[S:27])[C:5]([NH:10][CH3:11])=[N:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 67356496HCID 67356496, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86664891HCID 86664891, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

5-Bromo-6-methoxy-N-methyl-3-nitropyridin-2-amine (0.5 g, 1.9 mmol) in THF was combined with Raney nickel (70 mg) and hydrogenated in a Parr apparatus at ambient temperature for 10 h at 3.5 bar hydrogen pressure. Then the mixture was directly filtered into a mixture of 1,3-dichloro-2-isothiocyanatobenzene (0.39 g, 1.9 mmol) in THF and stirred overnight at ambient temperature. The solvent was removed i. vac. and the residue was purified by HPLC (C18 Symmetry, 8 μm, eluent: H2O+0.15% HCOOH+15-100% acetonitrile).

Workup

  1. customThe solvent was removed i
  2. customand the residue was purified by HPLC (C18 Symmetry, 8 μm, eluent: H2O+0.15% HCOOH+15-100% acetonitrile)

Sources & evidence

ORD record
ord-7a8320af200b4c44929c383761698a0d
Source dataset
uspto-grants-2014_04
Patent number
US08703796B2

Reaction notes

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