Triethylamine → N-hydroxybenzenecarboximidoyl chloride

HRID 606036ノート

反応式

HRID 606036 の反応式
[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

参加物

9

反応物 5

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6c3fa59e0ba04d1681709537664e23c7
出典データセット
uspto-grants-2011_03
特許番号
US07915281B2

反応ノート

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