Thionyl Chloride → (4-Nitrophthalimido)acetyl chloride

HRID 356155Notes

Reaction equation

HRID 356155 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH2:13][C:14](O)=[O:15])[C:8](=[O:9])[C:7]2=[CH:17][CH:18]=1)([O-:3])=[O:2].S(Cl)([Cl:21])=O>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH2:13][C:14]([Cl:21])=[O:15])[C:8](=[O:9])[C:7]2=[CH:17][CH:18]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2727372-(5-nitro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid

Product 1

HCID 15100608(4-Nitrophthalimido)acetyl chloride

Procedure

A mixture of (4-nitrophthalimido)acetic acid (2.17 g, 8.7 mmol) and thionyl chloride (5 mL) was refluxed for 80 minutes. The reaction mixture was cooled and, then, concentrated under reduced pressure to give a crude product of (4-nitrophthalimido)acetyl chloride. The crude product was dissolved, while heating, in 1,2-dichloroethane (10 mL). The solution was added (dropwise to a solution of (3aR*,10aS*)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one (2.30 g, 7.9 mmol) in 1,2-dichloroethane (10 mL). The mixture was stirred for 5 minutes at room temperatures, to which was added a saturated aqueous solution of sodium hydrogen carbonate (25 mL). The aqueous layer was separated. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, which was dried over magnesium sulfate, and them subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was crystallized from chloroform-ethanol-hexane to give 1.91 g (yield 46%) of the titled compound, m.p. 196.5°-197.5° C.

Workup

  1. temperaturewas refluxed for 80 minutes
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-523eed5d0d764e6282b0b14a999cc44a
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

Loading…