Hydrochloric Acid → 5-Chloro-N1-(4'-cyanophenyl)-2,4-dinitroaniline

HRID 1876450

반응식

HRID 1876450 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)#[N:16].CC(C)([O-])C.[K+].Cl>CN(C)C=O>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH:7]=1)[NH:21][C:20]1[CH:22]=[CH:23][C:17]([C:15]#[N:16])=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 133964-AminobenzonitrileHCID 772861,3-Dichloro-4,6-dinitrobenzeneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 706973965-Chloro-N1-(4'-cyanophenyl)-2,4-dinitroaniline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2,4-Dichloro-1,5-dinitrobenzene (II-1, 1.2 g, 5 mmol) and p-cyanoaniline (III-1, 0.59 g, 5 mmol) were dissolved in N,N-dimethylformamide (DFM, 10 ml). To the solution was added potassium tert-butoxide (1.4 g, 12.5 mmol) in batches in ice water bath. The mixture was allowed to react at room temperature for 45 minutes. The reaction liquid was poured into ice water. The pH value was adjusted to about 6 with dilute hydrochloric acid. The mixture was stirred for 30 minutes to precipitate a solid. The solid was filtered, washed with water to neutrality, dried, and separated on silica gel column (eluted with ethyl acetate: petroleum ether) to obtain a compound VI-1 (1.44 g, faint yellow solid). 1H NMR (CDCl3) δ ppm 7.41 (1H, s, ArH-6), 7.57 (2H, d, J=8.7 Hz, ArH-3′, 5′), 7.91 (2H, d, J=8.7 Hz, ArH-2′, 6′), 8.90 (1H, s, ArH-3), 10.07 (1H, s, NH).

후처리

  1. customto react at room temperature for 45 minutes
  2. customThe reaction liquid
  3. customto precipitate a solid
  4. filtrationThe solid was filtered
  5. washwashed with water to neutrality
  6. customdried
  7. customseparated on silica gel column (eluted with ethyl acetate: petroleum ether)
  8. customto obtain a compound VI-1 (1.44 g, faint yellow solid)

출처 및 근거

ORD 기록
ord-3438de63c1f34272bac3be02e2cce82c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309602B2

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