Triethylamine → N-hydroxybenzenecarboximidoyl chloride

HRID 606036Notes

Reaction equation

HRID 606036 reaction equation
[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

Participants

9

Reactant 5

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

Product 2

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6c3fa59e0ba04d1681709537664e23c7
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

Loading…