Ethanol → HCID 58626001, compound

HRID 131344Notes

Reaction equation

HRID 131344 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14](N)[C:13]3[CH:12]=[C:11]([CH3:17])[S:10][C:9]=3[NH:8][C:7]=2[CH:18]=1.CC[OH:21].C(=O)([O-])[O-].[K+].[K+]>O>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:15][C:14](=[O:21])[C:13]3[CH:12]=[C:11]([CH3:17])[S:10][C:9]=3[NH:8][C:7]=2[CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 692119036-Fluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

Product 1

HCID 58626001HCID 58626001, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82.5 °C

Procedure

Stir 6-fluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (82.5 g, 0.291 mol) as a suspension in deionized water (2475 mL) at ambient temperature. Add EtOH (830 mL) and stir for 15 minutes. Add potassium carbonate (301 g, 2.18 mol) with stirring and heat to gentle reflux (80-85° C.) for 3-4 days. Allow cooling to ambient temperature. Filter the product and rinse with 3:1/water:EtOH, then water. Dry the solid at 50-60° C. to give 55.2 g (76%) the title compound: 1H NMR (400 MHz, DMSO-d6) δ 9.18 (bs, 1H), 9.00 (bs, 1H), 6.90 (m, 1H), 6.73 (m, 1H), 6.60 (m, 2H), 2.24 (s, 3H). HRMS (ES) exact mass M+H calcd for C12H9FN2OS 249.0498; found 249.0488.

Workup

  1. temperatureheat
  2. temperatureAllow cooling to ambient temperature
  3. filtrationFilter the product
  4. washrinse with 3:1/water
  5. customDry the solid at 50-60° C.

Sources & evidence

ORD record
ord-a4f15e5352224c289f62410c72fedddb
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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