Triethylamine → N-hydroxybenzenecarboximidoyl chloride

HRID 606036노트

반응식

HRID 606036 반응식
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1C(=O)CCC1=O.C(N(CC)CC)C.[OH:25][N:26]=[C:27]([Cl:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH2:35]([N:38]1[C:50]2[C:49]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[N:43]=[C:42]([Cl:51])[C:41]=2[N:40]=[C:39]1[CH2:52][O:53][CH2:54][CH3:55])[CH:36]=[CH2:37]>CN(C=O)C.ClCCl>[OH:25][N:26]=[C:27]([Cl:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Cl:51][C:42]1[C:41]2[N:40]=[C:39]([CH2:52][O:53][CH2:54][CH3:55])[N:38]([CH2:35][CH:36]3[O:9][N:8]=[C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:37]3)[C:50]=2[C:49]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[N:43]=1

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 31398ChlorosuccinimideHCID 2756315N-hydroxybenzenecarboximidoyl chlorideHCID 860914521-allyl-4-chloro-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline

생성물 2

HCID 2756315N-hydroxybenzenecarboximidoyl chlorideHCID 866168714-chloro-2-(ethoxymethyl)-1-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

N-Hydroxybenzenecarboximidoyl chloride (13.7 g) was prepared according to the method described in Part D of Example 1 by reacting benzaldehyde oxime (11.5 g, 94.9 mmol) in DMF (20 mL) with N-chlorosuccinimide (12.6 g, 94.9 mmol) and was obtained as a white solid. Triethylamine (0.69 mL, 4.97 mmol) was added to a solution of N-hydroxybenzenecarboximidoyl chloride (644 mg, 4.14 mmol) and 1-allyl-4-chloro-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline (prepared as described in Part C of Example 1, 1.00 g, 3.32 mmol) in dichloromethane (50 mL) at room temperature. The solution was stirred overnight and then was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel to afford 4-chloro-2-(ethoxymethyl)-1-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline as a pale yellow solid (1.19 g).

후처리

  1. customwas obtained as a white solid
  2. washwas washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-6c3fa59e0ba04d1681709537664e23c7
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915281B2

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