Aniline → HCID 178496767, compound

HRID 1059450Notes

Reaction equation

HRID 1059450 reaction equation
CS[C:3](=[NH:22])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[S:13][C:12]3[N:14]=[CH:15][CH:16]=[N:17][C:11]=3[N:10]([CH2:18][O:19][CH3:20])[C:9]=2[CH:21]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1.CO>[C:24]1([NH:23][C:3](=[NH:22])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]3[S:13][C:12]4[N:14]=[CH:15][CH:16]=[N:17][C:11]=4[N:10]([CH2:18][O:19][CH3:20])[C:9]=3[CH:21]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 23565100HCID 23565100, compound

Product 1

HCID 178496767HCID 178496767, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

350 mg of methyl(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetothioimidate was dissolved in a solvent mixture of tetrahydrofuran (7 ml) with methanol (15 ml). After adding 0.5 ml of aniline, the resulting mixture was heated under reflux for 5 hours. Then the reaction mixture was brought back to room temperature. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia) to thereby give 250 mg of the title compound as yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customwas brought back to room temperature
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia)

Sources & evidence

ORD record
ord-5266a3076e8e41988c148c0b22214c21
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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