Phenyl isocyanate → Prinomide

HRID 127590

反応式

HRID 127590 の反応式
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:11])[CH2:8][C:9]#[N:10].C(N(CC)CC)C.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:11])[CH:8]([C:26](=[O:27])[NH:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]#[N:10]

参加物

5

反応物 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 27771703-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile

生成物 1

HCID 60352Prinomide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To the suspension of 1,135 g of 1-methyl-β-oxo-2-pyrrolpropionitrile in 17,000 ml of dry toluene, 913 g of anhydrous triethylamine are added, followed by 913 g of phenylisocyanate while stirring under nitrogen. The dark brown solution formed is stirred at room temperature overnight and evaporated at 60°-70°/10 mm Hg. The residue is taken up in 1,400 ml of methanol and the solution treated with 1,400 ml of 6 N hydrochloric acid in 4,200 ml of water. The suspension is cooled to 15°-20° for 20 minutes, filtered and the residue washed twice with 1,800 ml of water, twice with 1,000 ml of isopropanol and 13 times with 1,000 ml of diethyl ether. This crude residue is dried at 60° and 5 mm Hg to constant weight and 1,960 g thereof are dissolved in 44,400 ml of methylene chloride at room temperature. The solution is treated with 400 g of activated charcoal, filtered and the filtrate evaporated. The residue is triturated with 12,000 ml of anhydrous ethanol, the suspension filtered at 20°, washed 4 times with 1,000 ml of anhydrous ethanol and dried at 60° and 5 mm Hg, to yield the 1-methyl-β-oxo-α-phenylcarbamoyl-2-pyrrolpropionitrile melting at 172°-174°, it is identical with that of Examples 1, 6 or 9.

後処理

  1. additionare added
  2. customThe dark brown solution formed
  3. stirringis stirred at room temperature overnight
  4. customevaporated at 60°-70°/10 mm Hg
  5. additionthe solution treated with 1,400 ml of 6 N hydrochloric acid in 4,200 ml of water
  6. temperatureThe suspension is cooled to 15°-20° for 20 minutes
  7. filtrationfiltered
  8. washthe residue washed twice with 1,800 ml of water, twice with 1,000 ml of isopropanol and 13 times with 1,000 ml of diethyl ether
  9. dry with materialThis crude residue is dried at 60°
  10. dissolution5 mm Hg to constant weight and 1,960 g thereof are dissolved in 44,400 ml of methylene chloride at room temperature
  11. additionThe solution is treated with 400 g of activated charcoal
  12. filtrationfiltered
  13. customthe filtrate evaporated
  14. customThe residue is triturated with 12,000 ml of anhydrous ethanol
  15. filtrationthe suspension filtered at 20°
  16. washwashed 4 times with 1,000 ml of anhydrous ethanol
  17. customdried at 60°

出典と根拠

ORDレコード
ord-0b9fa9d19c4d450ba50956a70b1a483e
出典データセット
uspto-grants-1981_03
特許番号
US04256759

関連ノート

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