Lithium hydride → HCID 178425068、化合物

HRID 1154897ノート

反応式

HRID 1154897 の反応式
I.[NH:2]=[C:3]1[NH:7][CH2:6][CH2:5][NH:4]1.[H-].[Li+].[H][H].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[N:20]=[C:21]=[O:22]>CN(C)C=O>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[NH:20][C:21]([N:2]=[C:3]1[NH:7][CH2:6][CH2:5][NH:4]1)=[O:22]

参加物

6

反応物 4

HCID 62714Lithium hydrideHCID 2681232-Chloro-6-methylphenyl isocyanateHCID 178418361HCID 178418361、化合物HCID 178506595HCID 178506595、化合物

生成物 1

HCID 178425068HCID 178425068、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
5 °C

実験手順

A solution of 10.65 grams (0.05 mole) of 2-iminoimidazolidine hydroiodide in dimethylformamide is added dropwise with stirring over a 15 minute period to a cooled to 5° C. suspension of 397.5 milligrams (0.05 mole) of lithium hydride in 50 milliliters of dry dimethylformamide under nitrogen whereupon hydrogen evolution is observed. While stirring is continued, the mixture is allowed to gradually warm to room temperature. Thereafter, the reaction mixture is cooled to 0°-5° C. and a solution of 5.0 grams (0.03 mole) of 2-chloro-6-methylphenyl isocyanate in 25 milliliters of dry dimethylformamide is added dropwise over a two hour period. After completion of the addition, the mixture is allowed to warm gradually to room temperature while the stirring under nitrogen atmosphere is continued overnight to obtain the desired N-(2-chloro-6-methylphenyl)-N'-(2-imidazolidinylidene)urea product which remains in solution. The product is recovered from the reaction mixture by (a) adding the mixture to 300 milliliters of ice water with stirring, (b) lowering the pH below 2 with aqueous 10 percent hydrochloric acid to precipitate acid insoluble material (c) filtering, (d) basifying the filtrate to pH 8-9 with solid potassium carbonate, and (e) saturating the solution with solid sodium chloride to precipitate the desired N-(2-chloro-6-methylphenyl)-N'-(2-imidazolidinylidene)urea free base as a white solid. The product after washing thoroughly with water has a melting point of 169°-171° C.

後処理

  1. stirringWhile stirring
  2. temperatureto gradually warm to room temperature
  3. temperatureThereafter, the reaction mixture is cooled to 0°-5° C.
  4. additionAfter completion of the addition
  5. temperatureto warm gradually to room temperature while the stirring under nitrogen atmosphere
  6. waitis continued overnight

出典と根拠

ORDレコード
ord-254833c433ca4c549a3be851b47926bd
出典データセット
uspto-grants-1981_11
特許番号
US04298746

反応ノート

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