Aniline → HCID 21184374, compound

HRID 1385209Notes

Reaction equation

HRID 1385209 reaction equation
Cl[C:2]1[S:3][C:4]2[C:14](=[O:15])[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7](=[O:16])[C:5]=2[N:6]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[O:16]=[C:7]1[C:5]2[N:6]=[C:2]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[S:3][C:4]=2[C:14](=[O:15])[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2

Participants

4

Reactant 2

HCID 6115AnilineHCID 13769896HCID 13769896, compound

Product 1

HCID 21184374HCID 21184374, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 200 mg (0.8 mmol) of 2-chloro-4,9-dihydro-4,9-dioxo-naphtho[2,3-d]thiazole in 100 mL of ethanol, 730 μL (8 mmol) of aniline are added at 80° C. The reaction mixture is heated to reflux for 3.5 h; the red precipitate obtained is filtered after cooling, then purified on a cake (support: silica 6-35 μm; eluant: dichloromethane/heptane, 20/80 to 100/0, then dichloromethane/ethyl acetate, 99.5/0.5 to 0/100). The clean fractions are combined, then filtered through micropores; the solvent is evaporated at reduced pressure to produce 196 mg of 4,9-dihydro-4,9-dioxo-2-phenylamino-naphtho[2,3-d]thiazole in the form of red crystals.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3.5 h
  3. customthe red precipitate obtained
  4. filtrationis filtered
  5. temperatureafter cooling
  6. custompurified on a cake (support
  7. filtrationfiltered through micropores
  8. customthe solvent is evaporated at reduced pressure

Sources & evidence

ORD record
ord-9e03be9cde2644b5ba9ceb6a6c6abac6
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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