Acetic Acid → HCID 11999038, compound

HRID 1364109Notes

Reaction equation

HRID 1364109 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=O)[CH2:3]1.O.[NH2:20][NH2:21].CC(O)=O.C([O-])(O)=O.[Na+]>CCO>[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2/[C:4](=[N:20]/[NH2:21])/[CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 6222625,5-DiMethyl-2-(Morpholin-4-yl)-5,6-dihydro-1,3-benzothiazol-7(4H)-one

Product 1

HCID 11999038HCID 11999038, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of Example 48 (0.27 g, 1.00 mmol) in EtOH (10 mL) was added hydrazine monohydrate (0.05 g, 0.05 mL, 1.00 mmol) and a catalytic amount of AcOH. The reaction mixture was then heated to reflux for 8 h. Upon cooling, the reaction mixture was poured into aqueous sat. NaHCO3 (50 mL) and extracted with DCM (2×50 mL). The combined organic fractions were dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a white solid (0.10 g, 35%). δH (DMSO-d6) 5.93 (2H, br. s), 3.68 (4H, t, J 4.9 Hz), 3.36 (4H, t, J 4.9 Hz), 2.42 (2H, s), 2.22 (2H, s), 1.00 (6H, s). LCMS (ES+) 281.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 8 h
  3. temperatureUpon cooling
  4. extractionextracted with DCM (2×50 mL)
  5. dry with materialThe combined organic fractions were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-119520def65a4168b5db71d0d41e2d84
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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