Thionyl Chloride → 2-[[5-(Chloromethyl)-2-furanyl]methyl]-1H-isoindole-1,3(2H)-dione

HRID 65759Notes

Reaction equation

HRID 65759 reaction equation
O[CH2:2][C:3]1[O:7][C:6]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[CH:5][CH:4]=1.S(Cl)([Cl:22])=O>>[Cl:22][CH2:2][C:3]1[O:7][C:6]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 202132922-(5-Hydroxymethyl-2-furanylmethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 234521252-[[5-(Chloromethyl)-2-furanyl]methyl]-1H-isoindole-1,3(2H)-dione

Procedure

2-(5-Hydroxymethyl-2-furanylmethyl)-1H-isoindole-1,3(2H)-dione (10 g) was dissolved in thionyl chloride (15 ml) with the aid of gentle heat. The solution was evaporated to dryness and the solid residue re-evaporated with cyclohexanebenzene (1:1). The residue was suspended in ether, the suspension filtered, washed with ether and dried to give 2-(5-chloromethyl-2-furanylmethyl)-1H-isoindole-1,3(2H)-dione (10.1 g) m.p. 119°-122° (dec.). Analysis Found: C, 61.32; H, 3.71; N, 5.00. C14H10ClNO4 requires: C, 60.99; H, 3.66; N, 5.08%.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe solid residue re-evaporated with cyclohexanebenzene (1:1)
  3. filtrationthe suspension filtered
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-0fb6bf68411c45dfadbd4b9224866bc4
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

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