Hydrochloric Acid → 1-(p-Carboxybenzyl)-2-(1-imidazolyl)-3-methylindole

HRID 1719388

반응식

HRID 1719388 반응식
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].BrC[C:20]1[C:21]([C:26]([OH:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=1.Cl.[CH3:30]N(C)C=O>O>[C:26]([C:21]1[CH:20]=[CH:25][C:24]([CH2:30][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:1])=[C:3]2[N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:23][CH:22]=1)([OH:28])=[O:27]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide3회HCID 24758Sodium hydrideHCID 3460032-(Bromomethyl)benzoic acidHCID 132808392-(1-Imidazolyl)-3-methylindole

생성물 1

HCID 134914361-(p-Carboxybenzyl)-2-(1-imidazolyl)-3-methylindole

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 3-methyl-2-(1-imidazolyl)indole (1.50 g) in dimethylformamide (10 ml) is added dropwise to a suspension of 50% sodium hydride dispersion in mineral oil (0.77 g) in dimethylformamide (20 ml) stirred under nitrogen at 5°-10°. The suspension is stirred at 5°-10° for 1/2 hour. A solution of α-bromotoluic acid (1.63 g) in dimethylformamide (5 ml) is added dropwise to the suspension. The suspension is again stirred at 5°-10° for 1/2 hour and then overnight at room temperature. The suspension is diluted with water (100 ml) and acidified to pH 6 to 7 with 1N hydrochloric acid. The white precipitate which forms is collected by vacuum filtration, washed with water and dried to give 1-(p-carboxybenzyl)-2-(1-imidazolyl)-3-methylindole, m.p. 221°-5°. Recrystallization from acetonitrile gives crystals melting at 225°-7°.

후처리

  1. stirringThe suspension is stirred at 5°-10° for 1/2 hour
  2. stirringThe suspension is again stirred at 5°-10° for 1/2 hour
  3. customovernight
  4. customat room temperature
  5. filtrationThe white precipitate which forms is collected by vacuum filtration
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-64ee2ada45f34c5985bbb6b866e2ac32
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539410

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