Boron tribromide → 4-Isopropyl-6-hydroxysaccharin

HRID 129041

反応式

HRID 129041 の反応式
[CH:1]([C:4]1[CH:14]=[C:13]([O:15]C)[CH:12]=[C:11]2[C:5]=1[C:6](=[O:17])[NH:7][S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>>[OH:15][C:13]1[CH:12]=[C:11]2[C:5]([C:6](=[O:17])[NH:7][S:8]2(=[O:10])=[O:9])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:14]=1

参加物

4

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 101473624-Isopropyl-6-methoxysaccharin

生成物 1

HCID 100373464-Isopropyl-6-hydroxysaccharin収率 96%

実験手順

To a solution of 1.0 g (0.0039 mol) of 4-isopropyl-6-methoxysaccharin in 15 ml of MDC was added at ambient temperature 1.28 g (5.12 ml) of a 1M solution of boron tribromide in MDC. When addition was complete the reaction mixture was heated under reflux for about five hours, cooled, taken to dryness in vacuo and the residue treated with ice and saturated sodium bicarbonate. The aqueous solution was extracted once with ethyl acetate and then acidified to pH 1 with concentrated hydrochloric acid. Extraction of the mixture with ethyl acetate/diethyl ether (8:2), drying the organic extracts and removal of the solvent in vacuo afforded 0.9 g (96%) of 6-hydroxy-4-isopropylsaccharin as a white crystalline solid which was used as such in the next step.

後処理

  1. additionWhen addition
  2. temperaturewas heated
  3. temperatureunder reflux for about five hours
  4. temperaturecooled
  5. extractionThe aqueous solution was extracted once with ethyl acetate
  6. extractionExtraction of the mixture with ethyl acetate/diethyl ether (8:2)
  7. customdrying
  8. customthe organic extracts and removal of the solvent in vacuo

出典と根拠

ORDレコード
ord-a73040ecc88e4dcdaf4d2ee90b6ec695
出典データセット
uspto-grants-1995_11
特許番号
US05466701

関連ノート

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