Phosphorus pentachloride → 4-(1,3-Dioxoisoindolin-2-yl)cyclohexane-1-sulfonyl chloride

HRID 1483835Notes

Reaction equation

HRID 1483835 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][CH:15]([S:18]([OH:21])(=O)=[O:19])[CH2:14][CH2:13]1.P(Cl)(Cl)(Cl)(Cl)[Cl:23]>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][CH:15]([S:18]([Cl:23])(=[O:21])=[O:19])[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 893898864-(1,3-Dioxoisoindolin-2-yl)cyclohexane-1-sulfonic acid

Product 1

HCID 893896834-(1,3-Dioxoisoindolin-2-yl)cyclohexane-1-sulfonyl chlorideYield 69.3%

Procedure

A mixture of 4-(1,3-dioxoisoindolin-2-yl)cyclohexane-1-sulfonic acid (6.8 g, 22 mmol) and PCl5 (5 g, 24 mmol) was stirred at room temperature for 30 min. And then the mixture was heated at 100° C. and stirred for 2 h. After cooling to room temperature, the mixture was washed with EtOAc (150 mL×3). The combined extracts were concentrated in vacuo to give crude 4-(1,3-dioxoisoindolin-2-yl)cyclohexane-1-sulfonyl chloride (5 g, 68%) as a whit solid, which was used in the next step directly.

Workup

  1. temperatureAnd then the mixture was heated at 100° C.
  2. stirringstirred for 2 h
  3. temperatureAfter cooling to room temperature
  4. washthe mixture was washed with EtOAc (150 mL×3)
  5. concentrationThe combined extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-0cf178092f7e42b4962c5d3899a064b4
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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