Hydrochloric Acid → HCID 68294015, compound

HRID 1850068Notes

Reaction equation

HRID 1850068 reaction equation
Cl.[Cl:2][C:3]1[CH:20]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][C:4]=1[CH:5]=[C:6]1[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1>O1CCOCC1.O1CCOCC1.C(Cl)Cl>[NH:8]1[CH2:9][C:6](=[CH:5][C:4]2[CH:17]=[CH:18][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:20][C:3]=2[Cl:2])[CH2:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68294434HCID 68294434, compound

Product 1

HCID 68294015HCID 68294015, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 18626912Dioxane methylene chlorideSolvent

Procedure

A 4 M solution of HCl in dioxane (5 mL) was added to a solution of tert-butyl 3-(2-chloro-4-(methoxycarbonyl)benzylidene)azetidine-1-carboxylate (0.27 g, 0.66 mmol) in dioxane:DCM (1:1 v/v, 10 mL) and the mixture was stirred at room temperature for 3 h. Salt precipitation was observed. The reaction mixture was diluted with diethyl ether (20 mL). The precipitate was filtered, washed with ether and dried overnight to get the HCl salt of methyl 4-(azetidin-3-ylidenemethyl)-3-chlorobenzoate (0.12 g) as an off-white solid. ES+(M+H)+238

Workup

  1. customSalt precipitation
  2. additionThe reaction mixture was diluted with diethyl ether (20 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with ether
  5. customdried overnight

Sources & evidence

ORD record
ord-b65599f4f4f647838f5197bf1c9f1898
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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