N,N-Dimethylaniline → ethyl 4-acetamido-3-nitrobenzoate

HRID 2229447ノート

反応式

HRID 2229447 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18].CN(C)C1C=CC=CC=1.C1(C)C=CC=CC=1>O>[C:1]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 949N,N-DimethylanilineHCID 1140TolueneHCID 6367Acetyl chlorideHCID 3018687Benzoic acid, 4-amino-3-nitro-, ethyl ester

生成物 1

HCID 2826598ethyl 4-acetamido-3-nitrobenzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

Acetyl chloride (62 ml) was added dropwise to a mixture of ethyl 4-amino-3-nitrobenzoate (142 g), N,N-dimethylaniline (110 ml), and toluene (940 ml) in an ice bath. After stirring the mixture at 50° C. for 3 hours, it was cooled. Water (142 ml) was added thereto to stop the reaction. The toluene layer was separated and the organic layer was washed with dilute hydrochloric acid and successively with water. After the organic layer was concentrated to about 1/3 volume, hexane (284 ml) was added thereto for crystallization. Crystals were collected by filtration and washed with hexane to obtain the desired compound, ethyl 4-(acetylamino)-3-nitrobenzoate (157.7 g).

後処理

  1. temperatureit was cooled
  2. customthe reaction
  3. customThe toluene layer was separated
  4. washthe organic layer was washed with dilute hydrochloric acid and successively with water
  5. concentrationAfter the organic layer was concentrated to about 1/3 volume, hexane (284 ml)
  6. additionwas added
  7. customfor crystallization
  8. filtrationCrystals were collected by filtration
  9. washwashed with hexane

出典と根拠

ORDレコード
ord-e018559eb664419b8a2ae99d10378e22
出典データセット
uspto-grants-2002_07
特許番号
US06420409B1

反応ノート

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