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

HRID 1892473Notes

Reaction equation

HRID 1892473 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([NH:27][C:28](=[O:30])[CH3:29])[S:25][CH:26]=2)=[CH:16][CH:15]=1)=[O:11])[NH:2]C(OC(C)(C)C)=O.O1CCOCC1.[ClH:37]>ClCCl>[ClH:37].[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([NH:27][C:28](=[O:30])[CH3:29])[S:25][CH:26]=2)=[CH:18][CH:19]=1)=[O:11])[NH2:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86649981HCID 86649981, compound

Product 1

HCID 866499824-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl hydrazinecarboxylate hydrochlorideYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl tert-butyl hydrazine-1,2-dicarboxylate (203.0 mg, 0.467 mmol) in anhydrous dichloromethane (2.3 ml) was added 4M hydrogen chloride dioxane solution (2.3 ml, 9.2 mmol). After stirring at room temperature for 2.5 hr, the 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 filtered. The filtered product was washed with ethyl acetate and dried under reduced pressure to give the title compound (179.3 mg, quantitative) as a white solid.

Workup

  1. concentrationthe 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. filtrationfiltered
  6. washThe filtered product was washed with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-eeb3a8e140124b1f95614280c4b07c9b
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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