1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 86624670, compound

HRID 2075984Notes

Reaction equation

HRID 2075984 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[C:16](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:17]>ClCCl>[N:15]([C:5]1[CH:6]=[CH:7][C:8]([N:9]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]2)=[C:3]([O:2][CH3:1])[CH:4]=1)=[C:16]=[S:17]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 86624670HCID 86624670, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (203 mg, 1 mmol) and of 1,1′-thiocarbonyldi-2(1H)-pyridone (263 mg, 1.1 mmol) in dichloromethane (10 mL) was stirred at room temperature over night to yield an orange solution. The reaction was concentrated under reduced pressure to ¼ of its volume and directly purified on silica gel using dichloromethane/methanol (95:5 v/v) as eluent to yield the title compound (230 mg, 94%) as a yellow oil, which solidifies on standing. MS ISP (m/e): 246.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.67 (s, 1H), 7.21 (d, 1H), 6.91-6.86 (m, 3H), 3.86 (s, 3H), 2.29 (s, 3H).

Workup

  1. customto yield an orange solution
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customdirectly purified on silica gel

Sources & evidence

ORD record
ord-e8b3f654845841bea54114d623260f83
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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