Triethylamine → N-Methyl-N-methoxy-2-(1-triphenylmethyl-1H-imidazol-4-yl)acetamide

HRID 342121

반응식

HRID 342121 반응식
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([OH:9])=O)[N:3]=[CH:2]1.[C:10]1([C:16](Br)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([N:32]([CH2:35]C)CC)C.Cl.CN(C)CCCN=C=NCC.[C:49](=O)(O)[O-:50].[Na+]>CN(C)C=O.O>[CH3:35][N:32]([O:50][CH3:49])[C:7](=[O:9])[CH2:6][C:4]1[N:3]=[CH:2][N:1]([C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 11692BromotriphenylmethaneHCID 96215Imidazole-4-acetic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 54243787N-Methyl-N-methoxy-2-(1-triphenylmethyl-1H-imidazol-4-yl)acetamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-imidazoleacetic acid (1.04 g, 6.40 mmol) and triphenylmethyl bromide (2.48 g, 7.68 mmol) in dimethylformamide (40 ml) was added triethylamine (4.46 ml, 32 mmol) and the suspension allowed to stir for 18 hours at room temperature. After this time, the mixture was treated with 3-hydroxy-1,2,3-benzotriazin-4(3)-one (HOOBT) (1.31 g, 8 mmol), N, O-dimethylhydroxyamine hydrochloride (1.56 g, 16 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (1.53 g, 8 mmol) and stirred for 24 hours at room temperature. After this time, sat. aq. sodium bicarbonate (50 ml) and water (50 ml) were added and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with sat. aq. NaHCO3 (100 ml) and then brine (50 ml) and the solvent evaporated in vacuo. The residue was suspended in ether (20 ml) and the white solid filtered to give the title compound as a white solid. 1NMR(CD3OD, 300 MHz) δ 7.37(10H, m), 7.16(6H, m), 6.84(1H, s), 3.73(2H, s), 3.68(3H, s) and 3.18(3H, s)ppm.

후처리

  1. stirringstirred for 24 hours at room temperature
  2. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  3. washThe combined extracts were washed with sat. aq. NaHCO3 (100 ml)
  4. custombrine (50 ml) and the solvent evaporated in vacuo
  5. filtrationthe white solid filtered

출처 및 근거

ORD 기록
ord-b17ad3e9309c4c468864fcd3b06c7b39
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856326

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