Hydrochloric Acid → N-(2-fluorophenyl)-2-oxo-2,3-dihydro-3-benzo[b]thiophenecarboxamide

HRID 443601ノート

反応式

HRID 443601 の反応式
[O:1]=[C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[CH2:3]1.[H-].[Na+].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=O)[O:22]C1C=CC=CC=1.Cl>CN(C)P(=O)(N(C)C)N(C)C>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([CH:3]1[C:2](=[O:1])[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]1=2)=[O:22]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 591560Benzo[b]thiophen-2(3H)-oneHCID 3790948phenyl N-(2-fluorophenyl)carbamate

生成物 1

HCID 12799381N-(2-fluorophenyl)-2-oxo-2,3-dihydro-3-benzo[b]thiophenecarboxamide

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒2 回

実験手順

A solution of 50 g of 2,3-dihydro-2-oxo-benzo[b]thiophene in 200 ml of hexamethylphosphoric acid triamide is added dropwise to a suspension of 16 g of a 50% strength sodium hydride/mineral oil dispersion in 500 ml of hexamethylphosphoric acid triamide, whilst cooling, the temperature being kept below 15°. After stirring for one hour at room temperature, 77 g of phenyl N-(2-fluorophenyl)-carbamate are added in portions, with external cooling. The reaction mixture is stirred for a further 16 hours at room temperature and poured into a mixture of 300 ml of 2 N hydrochloric acid and 3,000 ml of ice water. An oil separates out and this crystallises after about 2 hours. The crystalline product, in which solvent is incorporated, is dissolved in 1,000 ml of diethyl ether and the solution is washed with water. The organic phase is separated off, dried over sodium sulphate and evaporated to dryness. The crude product is recrystallised from diethyl ether and gives N-(2-fluorophenyl)-2-oxo-2,3-dihydro-3-benzo[b]thiophenecarboxamide, melting point 155°-156°.

後処理

  1. temperaturewhilst cooling
  2. custombeing kept below 15°
  3. stirringThe reaction mixture is stirred for a further 16 hours at room temperature
  4. customthis crystallises after about 2 hours
  5. dissolutionis dissolved in 1,000 ml of diethyl ether
  6. washthe solution is washed with water
  7. customThe organic phase is separated off
  8. dry with materialdried over sodium sulphate
  9. customevaporated to dryness
  10. customThe crude product is recrystallised from diethyl ether

出典と根拠

ORDレコード
ord-a4c51d4d8661457f8e48e437c76e1230
出典データセット
uspto-grants-1981_04
特許番号
US04260779

反応ノート

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