Dichlone → 2-(Methylamino)naphtho[2,3-d][1,3]thiazole-4,9-dione

HRID 579157Notes

Reaction equation

HRID 579157 reaction equation
Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[CH:8][CH:7]=[CH:6][CH:5]=2.C([O-])([O-])=O.[K+].[K+].[CH3:21][NH:22][C:23]([NH2:25])=[S:24]>C(O)(C)C>[CH3:21][NH:22][C:23]1[S:24][C:11]2[C:10](=[O:13])[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3](=[O:14])[C:2]=2[N:25]=1

Participants

5

Reactant 3

HCID 8342DichloneHCID 11430Potassium CarbonateHCID 2723704Methylthiourea

Product 1

HCID 665216742-(Methylamino)naphtho[2,3-d][1,3]thiazole-4,9-dioneYield 0.93%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2,3-dichloronaphthalene-1,4-dione 10.0 g (0.044 mol,), 18.0 g K2CO3 (0.13 mol, 3.0 eq) and 1-methylthiourea (0.056 mol, 1.2 eq) in 100 ml isopropanol was stirred at room temperature under N2 for 20 h. After removing all solvents under reduced pressure, the residue was diluted with CH2Cl2 and the K2CO3 was removed by filtration, the organic layer was concentrated, the residue was purified by chromatography to afford 0.1 g 2-(methylamino-) naphtho[2,3-d]thiazole-4,9-dione as black solid in a yield of 0.93%. 1HNMR (300 MHz, DMSO) δ3.59 (s, 3H); 7.78-7.81 (m, 2H); 7.89-7.93 (m, 1H); 7.98-8.01 (m, 1H); 9.06 (br, 1H) ppm. MS-ESI: cal. 244; found: 285 (M+Na+H2O).

Workup

  1. customAfter removing all solvents under reduced pressure
  2. additionthe residue was diluted with CH2Cl2
  3. customthe K2CO3 was removed by filtration
  4. concentrationthe organic layer was concentrated
  5. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-04b62e796d7e4c36a55f9d83f83a5d3a
Source dataset
uspto-grants-2015_05
Patent number
US09040713B2

Reaction notes

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