Nitric Acid → 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5-nitro-2(3H)-benzothiazolone

HRID 1199618

反応式

HRID 1199618 の反応式
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH2:10][C:11]3[N:15]=[C:14]([CH3:16])[O:13][N:12]=3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[N+:24]([O-])([OH:26])=[O:25]>C(OCC)(=O)C>[F:1][C:2]1[C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:5]2[N:6]([CH2:10][C:11]3[N:15]=[C:14]([CH3:16])[O:13][N:12]=3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 199794996-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone

生成物 1

HCID 199794886-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5-nitro-2(3H)-benzothiazolone収率 96.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A compound of 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone (11.5 g) was added portionwise to concentrated sulfuric acid (200 g) which had been cooled to a temperature of 5° to 10° C. The reaction mixture was stirred at a temperature of 0° to 5° C. for 10 minutes. To the reaction mixture was dropwise added a 98% nitric acid (3 g). The reaction mixture was stirred at a temperature of 0° to 5° C. for 2 hours, and then poured onto ice. Ethyl acetate (1 liter) was added to the mixture, and the whole was stirred. The ethyl acetate layer was separated, washed with water, with a saturated aqueous sodium bicarbonate solution, and then with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from ethanol, so that the aimed product, i.e. 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5 -nitro-2(3H)-benzothiazolone (13.0 g) was obtained. m.p. 192°-193° C.

後処理

  1. temperaturehad been cooled to a temperature of 5° to 10° C
  2. stirringThe reaction mixture was stirred at a temperature of 0° to 5° C. for 2 hours
  3. additionpoured onto ice
  4. stirringthe whole was stirred
  5. customThe ethyl acetate layer was separated
  6. washwashed with water, with a saturated aqueous sodium bicarbonate solution
  7. dry with materialwith a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was recrystallized from ethanol, so that the aimed product

出典と根拠

ORDレコード
ord-3e957c0a09264b06bae7c37b88a4590e
出典データセット
uspto-grants-1990_02
特許番号
US04902335

関連ノート

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