Hydrochloric Acid → HCID 67790043、化合物

HRID 973673ノート

反応式

HRID 973673 の反応式
ClC1C=CC(C(NN)=O)=CC=1.C(N=C=O)C.[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([C:22]([NH:24][NH:25][C:26]([NH:28][CH2:29][CH3:30])=[O:27])=O)=[CH:20][CH:19]=1.NNC(N)=O.Cl>O1CCCC1.[OH-].[Na+]>[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([CH:22]2[N:28]([CH2:29][CH3:30])[C:26](=[O:27])[N:25]=[N:24]2)=[CH:20][CH:19]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 5196SemicarbazideHCID 8022Ethyl isocyanateHCID 108164-ChlorobenzohydrazideHCID 13864336HCID 13864336、化合物

生成物 1

HCID 67790043HCID 67790043、化合物収率 93.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
10 °C

実験手順

To a suspension of 4-chlorobenzhydrazide (98.5 g, 0.05 mole) in tetrahydrofuran (100 ml) at room temperature ethylisocyanate (4.2 g, 0.05 mole) was added slowly with magnetic stirring. The reaction was slightly exothermic and the reaction mixture turned to a thick paste. Stirring was continued an additional 30 min after which the solid was collected by suction-filtration and washed with a small amount of tetrahydrofuran and dried to provide 11.6 g (96.6% yield), of 1-(4-chlorobenzoyl)-4-ethyl semicarbazide as a white solid, m.p. 242°-243° C. The above semicarbazide (10 g, 0.0414 mole) was dissolved in 1N sodium hydroxide solution (100 ml) and was refluxed with stirring for 16 hr. The solution was cooled down to about 10° C. by an ice bath and was neutralized by conc. hydrogen chloride until pH 2. The resultant white solid was collected by suction-filtration and washed with water to give 8.65 g (93.5% yield) of 3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one as a white solid. m.p. 190°-197° C. A proton NMR spectrum was consistent with the desired structure.

後処理

  1. additionwas added slowly with magnetic stirring
  2. filtrationafter which the solid was collected by suction-filtration
  3. washwashed with a small amount of tetrahydrofuran
  4. customdried
  5. customto provide 11.6 g (96.6% yield)
  6. temperaturewas refluxed
  7. stirringwith stirring for 16 hr
  8. filtrationThe resultant white solid was collected by suction-filtration
  9. washwashed with water

出典と根拠

ORDレコード
ord-a8ee1e53ec674d949c1afc9369001932
出典データセット
uspto-grants-1991_11
特許番号
US05064845

反応ノート

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