4-Chloroaniline → 4'-Chloro-3-hydroxy-2-nitrobenzanilide

HRID 1784894

반응식

HRID 1784894 반응식
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([OH:1])[C:3]=2[N+:11]([O-:13])=[O:12])=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 78124-ChloroanilineHCID 757711-HydroxybenzotriazoleHCID 2932913-Hydroxy-2-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 178569794'-Chloro-3-hydroxy-2-nitrobenzanilide수율 92.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Hydroxy-2-nitrobenzoic acid (2.00 g) was dissolved in 110 ml of N,N-dimethylformamide, then 1.53 g of 4-chloroaniline, 3.15 g of 1-ethyl-3-[3-(N,N-dimethylamino) propyl]carbodiimide hydrochloride and 2.21 g of 1-hydroxybenzotriazole were added thereto and the mixture was stirred at room temperature for 4 days. The reaction solution was concentrated in vacuo, a saturated saline was added to the concentrate and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by means of a silica gel column chromatography using chloroform:methanol (100:1) as an eluate to give 2.97 g of 4′-chloro-3-hydroxy-2-nitrobenzanilide.

후처리

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additiona saturated saline was added to the
  3. concentrationconcentrate
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by means of a silica gel column chromatography

출처 및 근거

ORD 기록
ord-4cfcc01f8e9d4cd8be424b588c6114d4
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504417B2

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