Sulfuryl chloride → HCID 14348768, compound

HRID 414341Notes

Reaction equation

HRID 414341 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]4[O:18][CH:17]([CH2:19][OH:20])[CH2:16][C:15]=4[C:10]=3[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:24])(=O)=O>C(Cl)Cl>[Cl:24][C:13]1[C:14]2[O:18][CH:17]([CH2:19][OH:20])[CH2:16][C:15]=2[C:10]2[O:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 14128049HCID 14128049, compound

Product 1

HCID 14348768HCID 14348768, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A portion (10 g) of the 7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-methanol prepared in Example 1 was dissolved in 300 ml of methylene chloride. To the ice-cooled solution, sulfuryl chloride (9 g) was added over time under agitation. The mixture was thereafter stirred for 8 hours at room temperature. The solvent was distilled off and the resulting residue was purified by column chromatography using methylene chloride as an eluant, whereupon 3.3 g of 5-chloro-7,8-dihydro-3-phenylfuro[2,3-g]-1,2benzisoxazole-7-methanol was obtained. This compound (3.3 g) was dissolved in 100 ml of acetone and, to the stirred solution, a mixture of chromium (VI) oxide (4 g), water (6 ml) and concentrated sulfuric acid (5.9 g) was added dropwise over time, and the solution was stirred for 2.5 hours at room temperature. The insolubles were filtered off by suction. After distilling off the acetone, water was added to the residue and the mixture was subjected to extraction with ether. The ether layer was washed with water and dried, followed by distilling off of the solvent. The residue was recrystallized with acetonitrile to yield 1 g of 5-chloro-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 221°-224° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 315.

Workup

  1. additionwas added over time under agitation
  2. distillationThe solvent was distilled off
  3. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-47e03f1dd92d4426ae8f823714f8ff7e
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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