2-Furancarbonyl chloride → 2-(2-Furoyl)-3-oxo-1,2-benzisothiazoline-6-carboxylic acid methyl ester

HRID 1701802Notes

Reaction equation

HRID 1701802 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[CH3:9][O:10][C:11]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[NH:18][S:19][C:15]=2[CH:14]=1)=[O:12].[Na]>O1CCCC1>[CH3:9][O:10][C:11]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[N:18]([C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[O:7])[S:19][C:15]=2[CH:14]=1)=[O:12]

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 5360545SodiumHCID 19076707Methyl 3-Hydroxybenzo[d]isothiazole-6-carboxylate

Product 1

HCID 543616282-(2-Furoyl)-3-oxo-1,2-benzisothiazoline-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-furoyl chloride (0.1 mole) and 3-oxo-1,2-benzisothiazoline-6-carboxylic acid methyl ester, 1,1-dioxide, sodium salt, from example 3C, above, is refluxed in 100 ml of tetrahydrofuran for 3 hours. The reaction mixture is filtered hot and the filtrate is concentrated to give the product. The product is triturated with ether and air dried to give 2-(2-furoyl)-3-oxo-1,2-benzisothiazoline-6-carboxylic acid methyl ester, 1,1-dioxide.

Workup

  1. filtrationThe reaction mixture is filtered hot
  2. concentrationthe filtrate is concentrated
  3. customto give the product
  4. customThe product is triturated with ether and air
  5. customdried

Sources & evidence

ORD record
ord-819bb72c2d9d4f309cbff44ce71cedba
Source dataset
uspto-grants-1980_03
Patent number
US04195023

Reaction notes

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