Hydrochloric Acid → HCID 66572070, compound

HRID 75761

Reaction equation

HRID 75761 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].Cl[C:19]1[S:20][C:21]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=2[N:23]=1.Cl.O1CCOCC1>CCO>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:19]3[S:20][C:21]4[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][CH:16]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 20498702-Chloro-6-fluorobenzothiazoleHCID 53407704Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate

Product 1

HCID 66572070HCID 66572070, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the compound of step 2 (3.0 g; 12.9 mmol) and 2-chloro-6-fluoro benzothiazole (2.67 g; 14.2 mmol) in EtOH (60 ml) was heated at 60° C. to get a clear solution. To the hot solution 4N HCl in dioxane (1.6 ml; 6.45 mmol) was added and the resulting reaction mixture was refluxed for 20 hours. The reaction mixture was cooled to room temperature and the solid was filtered, and washed with EtOH (2×10 ml). The solid was dried under vacuum to yield 2.83 g (57.2%) of the title compound. Mass (ES−) 382 (M−1); IR (KBr): 3410 (br), 2710 (br), 1729, 1719, 1630, 1598; 1H NMR (DMSO-d6): δ 1.36 (t, 3H), 4.41 (q, 2H), 7.20 (m, 1H), 7.67 (m, 1H), 7.78 (m, 1H), 7.81 (s, 1H), 7.87-7.99 (m, 4H), 10.92 (br, 1H).

Workup

  1. customto get a clear solution
  2. customthe resulting reaction mixture
  3. temperaturewas refluxed for 20 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationthe solid was filtered
  6. washwashed with EtOH (2×10 ml)
  7. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-2647f0bac3b145bd852a4c4eb90cde0d
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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