1,4-Dioxane hydrochloride → 4-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl hydrazinecarboxylate hydrochloride

HRID 1892471Notes

Reaction equation

HRID 1892471 reaction equation
[NH:1]([C:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]2[N:22]=[C:23]([NH:26][C:27](=[O:29])[CH3:28])[S:24][CH:25]=2)=[CH:15][CH:14]=1)=[O:11])[NH:2]C(OC(C)(C)C)=O.O1CCOCC1.[ClH:36]>ClCCl>[ClH:36].[NH:1]([C:10]([O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][C:21]2[N:22]=[C:23]([NH:26][C:27](=[O:29])[CH3:28])[S:24][CH:25]=2)=[CH:17][CH:18]=1)=[O:11])[NH2:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 866499784-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl tert-butyl hydrazine-1,2-dicarboxylate

Product 1

HCID 866499794-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl hydrazinecarboxylate hydrochlorideYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl tert-butyl hydrazine-1,2-dicarboxylate (445.2 mg, 1.06 mmol) in anhydrous dichloromethane (5.3 ml) was added 4M hydrogen chloride dioxane solution (5.3 ml, 21.3 mmol). After stirring at room temperature for 2 hr, the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the concentrated residue, and the mixture was concentrated again under reduced pressure. This operation was performed 3 times to remove hydrogen chloride gas azeotropically. The residue was suspended in ethyl acetate, and the solid was collected by filtration, washed twice with ethyl acetate, and dried under reduced pressure to give the title compound (380.5 mg, quantitative) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the concentrated residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. customto remove hydrogen chloride gas azeotropically
  5. filtrationthe solid was collected by filtration
  6. washwashed twice with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-7bf8475ec6bf4b959787fd7323278f6e
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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