Thionyl Chloride → HCID 86685933, compound

HRID 2277606Notes

Reaction equation

HRID 2277606 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[CH:17]=[N:18][CH:19]=[C:20]([CH2:22]O)[CH:21]=1)[C:9]2([CH3:25])[CH3:24]>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[CH:17]=[N:18][CH:19]=[C:20]([CH2:22][Cl:3])[CH:21]=1)[C:9]2([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86685932HCID 86685932, compound

Product 1

HCID 86685933HCID 86685933, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3.5 °C

Procedure

Thionyl chloride (1.4 mL, 19.0 mmol) was added slowly at 0° C. to a solution of 5-chloro-2-(5-hydroxymethyl-pyridin-3-yl)-3,3-dimethyl-2,3-dihydro-isoindol-1-one (1.14 g, 3.8 mmol) in DCM (50 mL). After the addition, the reaction mixture was stirred at 2-5° C. for 2 hours before it was poured into satd. aq. NaHCO3 solution (50 mL) and extracted with EtOAc (2×150 mL). The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (1.42 g, 92%) as a light yellowish solid. MS: 322.1 (M+H+).

Workup

  1. additionAfter the addition
  2. additionwas poured into satd
  3. extractionaq. NaHCO3 solution (50 mL) and extracted with EtOAc (2×150 mL)
  4. washThe organic layer was washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f1a562041ad4e859794601b91cba4cd
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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