2-Methylamino-5-nitrobenzophenone → Nimetazepam

HRID 1729968

反応式

HRID 1729968 の反応式
[N:1]([CH2:4][C:5](Cl)=[O:6])=C=O.[CH3:8][NH:9][C:10]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O>O>[CH3:8][N:9]1[C:10]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:1][CH2:4][C:5]1=[O:6]

参加物

4

反応物 2

HCID 786612-Methylamino-5-nitrobenzophenoneHCID 132291762-Isocyanatoacetyl chloride

生成物 1

HCID 4496Nimetazepam

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
95 °C

実験手順

2-Milliliters of 2-isocyanatoacetyl chloride was cooled, and 0.20 g. of powdered 2-methylamino-5-nitrobenzophenone was added thereto with stirring. After stirring the resulting mixture at room temperature for one hour, excess 2-isocyanatoacetyl chloride was removed by reduced pressure distillation. To the residue was added 4 ml. of pyridine, whereby a reaction took place with generation of heat. The reaction liquid was heated at 95° C, for 1.5 hours, diluted with water and then extracted with chloroform. The chloroform layer was washed with a 5% aqueous hydrochloric acid solution and then with an aqueous sodium chloride solution in this order, dried over Glauber's salt, and evaporated by reduced pressure distillation. Subsequently, the residue was chromatographically purified (solvent: chloroform→ethyl acetate) by use of a column packed with 10 g. of silica gel to obtain 1-methyl-5-phenyl-7-nitro-1,3-dihydro-2H-1,4-benzodiazepin-2-one having a melting point of 154° to 156° C.

後処理

  1. stirringAfter stirring the resulting mixture at room temperature for one hour
  2. customexcess 2-isocyanatoacetyl chloride was removed by reduced pressure distillation
  3. additionTo the residue was added 4 ml
  4. temperatureof heat
  5. customThe reaction liquid
  6. extractionextracted with chloroform
  7. washThe chloroform layer was washed with a 5% aqueous hydrochloric acid solution
  8. dry with materialwith an aqueous sodium chloride solution in this order, dried over Glauber's salt
  9. customevaporated by reduced pressure distillation
  10. customSubsequently, the residue was chromatographically purified (solvent: chloroform→ethyl acetate) by use of a column

出典と根拠

ORDレコード
ord-442193375f16488eb44e92ef81577abc
出典データセット
uspto-grants-1976_11
特許番号
US03991048

関連ノート

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