Acetic Acid → HCID 69738282、化合物

HRID 1582421ノート

反応式

HRID 1582421 の反応式
[CH:1]([N:4]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[C:5](=[O:10])[CH2:6][C:7](=O)[CH3:8])([CH3:3])[CH3:2].C(O)(=O)C.[NH3:28]>C(OCC)(=O)C>[CH:1]([N:4]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[C:5](=[O:10])/[CH:6]=[C:7](\[NH2:28])/[CH3:8])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 222Ammonia2 回HCID 22320826HCID 22320826、化合物

生成物 1

HCID 69738282HCID 69738282、化合物収率 91%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
35 °C

実験手順

N-Isopropyl-3-oxo-N-[4-(phenylamino)phenyl]butyramide (30.0 g, 0.0967 mol) and conc. acetic acid (1.4 g, 0.0233 mol) in ethyl acetate (140 g) were introduced into an autoclave. Ammonia (16.0 g, 0.9395 mol) was introduced in the course of 10 minutes and the temp. of the reaction mixture was increased to 35° C. during this period. After the introduction a pressure of 14 bar is present. The temperature of the reaction mixture was heated to 70° C. in the course of 30 min. In the course of this, the pressure rose to 17 bar. After 2.5 h under these conditions, the reaction mixture was cooled to 25° C. and ammonia was released. The reaction mixture was further cooled to 5° C. in order to crystallize the product. The suspension was filtered. The pale grey solid was washed with cold (0° C.) ethyl acetate (20 ml) and dried in vacuo (50 mbar) at 35° C. for 2 days. (Z)-3-Aminobut-2-enoic acid N-isopropyl-N-[4-(phenylamino)phenyl]amide (27.2 g, 91.0%) was obtained.

後処理

  1. temperatureThe temperature of the reaction mixture was heated to 70° C. in the course of 30 min
  2. temperaturethe reaction mixture was cooled to 25° C.
  3. temperatureThe reaction mixture was further cooled to 5° C. in order
  4. customto crystallize the product
  5. filtrationThe suspension was filtered
  6. washThe pale grey solid was washed with cold (0° C.) ethyl acetate (20 ml)
  7. customdried in vacuo (50 mbar) at 35° C. for 2 days

出典と根拠

ORDレコード
ord-72ce4fa0c98c47ac977cb4da60344819
出典データセット
uspto-grants-2004_05
特許番号
US06734324B2

反応ノート

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