Thionyl Chloride → Tert-butyl 3-[3-(1-chloroethyl)-6-cyano-2-methoxy-5-methylphenyl]azetidine-1-carboxylate

HRID 1499912Notes

Reaction equation

HRID 1499912 reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH:10](O)[CH3:11])=[C:5]([O:13][CH3:14])[C:4]=1[CH:15]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1)#[N:2].S(Cl)([Cl:28])=O>C(Cl)Cl.CN(C)C=O>[Cl:28][CH:10]([C:6]1[C:5]([O:13][CH3:14])=[C:4]([CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[C:3]([C:1]#[N:2])=[C:8]([CH3:9])[CH:7]=1)[CH3:11]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 86677832HCID 86677832, compound

Product 1

HCID 86677833Tert-butyl 3-[3-(1-chloroethyl)-6-cyano-2-methoxy-5-methylphenyl]azetidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The tert-butyl 3-[2-cyano-5-(1-hydroxyethyl)-6-methoxy-3-methylphenyl]azetidine-1-carboxylate (2.1 g, 6.4 mmol) was taken up in methylene chloride (50.0 mL) and N,N-dimethylformamide (0.59 mL), cooled in an ice bath and the thionyl chloride (0.56 mL, 7.7 mmol) was added slowly. After stirring for 2 hrs the reaction was complete by LC/MS and was partitioned between ethyl acetate and water. The combined organic layer was washed with water saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to give crude tert-butyl 3-[3-(1-chloroethyl)-6-cyano-2-methoxy-5-methylphenyl]azetidine-1-carboxylate as an oil (2.2 g, 100%). LCMS calculated for C15H18ClN2O3(M+H)+: m/z=309.1; found: 309.1.

Workup

  1. customwas partitioned between ethyl acetate and water
  2. washThe combined organic layer was washed with water saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8d74fc8a502a4c62a9113a4960bb3306
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…