Methyl isothiocyanate → HCID 9902990, compound

HRID 1977426Notes

Reaction equation

HRID 1977426 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([NH2:16])=[CH:15][C:8]=23)=[CH:4][CH:3]=1.[CH3:19][N:20]=[C:21]=[S:22]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([NH:16][C:21]([NH:20][CH3:19])=[S:22])=[CH:15][C:8]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 9814184HCID 9814184, compound

Product 1

HCID 9902990HCID 9902990, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A solution of obtained amine from Example 263 (150 mg, 0.542 mmol) in 5 mL of pyridine was treated with methyl isothiocyanate (198 mg, 2.71 mmol). The solution heated to 100° C. under a nitrogen atmosphere for 5 days. All volatiles were removed under reduced pressure. The resulting product was purified by flash column chromatography on silica gel eluting with chloroform/NH4OH, affording 110 mg (58.1%) of the title compound.

Workup

  1. customAll volatiles were removed under reduced pressure
  2. customThe resulting product was purified by flash column chromatography on silica gel eluting with chloroform/NH4OH

Sources & evidence

ORD record
ord-f04adf14ed01483b84c86559ee45f79f
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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