Thionyl Chloride → HCID 20296664, compound

HRID 1389513Notes

Reaction equation

HRID 1389513 reaction equation
O[C:2]([CH3:15])([CH3:14])[CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[NH:5]1.S(Cl)([Cl:18])=O>>[Cl:18][C:2]([CH3:15])([CH3:14])[CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[NH:5]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12901821HCID 12901821, compound

Product 1

HCID 20296664HCID 20296664, compound

Procedure

1,3-Dihydro-3-(2-hydroxy-2-methylpropyl)-2H-isoindol-1-one (12 g, described in Example 2) is added portionwise to thionyl chloride (72 ml) while stirring at room temperature. After 2 hr the reaction is evaporated and the residue is chromatographed on silica gel using acetone-toluene (3:7). The eluates are evaporated and crystallized from ethyl acetate-diethyl ether to give the title compound (2.2 g); mp 153°-155° C. and Anal. Calcd for C12H14ClNO: C, 64.43% H, 6.31% N, 6.27% and Found: 64.25% H, 6.26% N, 6.17%.

Workup

  1. customAfter 2 hr the reaction is evaporated
  2. customthe residue is chromatographed on silica gel
  3. customThe eluates are evaporated
  4. customcrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-5c97269b18bd4ebbb02bbf25b95adea8
Source dataset
uspto-grants-1981_01
Patent number
US04244966

Reaction notes

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