Dicyclohexylcarbodiimide → N-[p-(3-methylbutoxy)benzyl]-2-(3-pyridyl)thiazolidine-4-carboxamide

HRID 704435

반응식

HRID 704435 반응식
[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]2[NH:25][CH:24]([C:26](O)=[O:27])[CH2:23][S:22]2)[CH:16]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][NH:11][C:26]([CH:24]2[CH2:23][S:22][CH:21]([C:17]3[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=3)[NH:25]2)=[O:27])=[CH:12][CH:13]=1

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 8084254-(3-Methyl-butoxy)-benzylamine

생성물 1

HCID 15306325N-[p-(3-methylbutoxy)benzyl]-2-(3-pyridyl)thiazolidine-4-carboxamide수율 97.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1.13 g of p-(3 methylbutoxy)benzylamine, 1.29 g of 2-(3-pyridyl)thiazolidine-4-carboxylic acid, 1.25 g of dicyclohexylcarbodiimide and 0.82 g of 1-hydroxybenzotriazole in 20 ml of N,N-dimethylformamide was stirred overnight at room temperature. The reaction mixture was diluted with 100 ml of ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure Purification of the thus-obtained residue by silica gel column chromatography (eluent: ethyl acetate) gave 2.20 g of N-[p-(3-methylbutoxy)benzyl]-2-(3-pyridyl)thiazolidine-4-carboxamide. To a solution of this compound in 60 ml of ethyl acetate was added 4 ml of 4N hydrogen chloride solution in dioxane. The precipitate solid was collected by filtration, washed with ethyl acetate and dried under reduced pressure to give 2.30 g of N-[p-(3-methylbutoxy)benzyl]-2-(3-pyridyl)thiazolidine-4-carboxamide dihydrochloride. Melting point 120°-128° C.

후처리

  1. filtrationthe insoluble matter was filtered off
  2. washThe filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure Purification of the thus-obtained residue by silica gel column chromatography (eluent: ethyl acetate)

출처 및 근거

ORD 기록
ord-e4529035614741248b3c2d5fb4b1f7cb
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04987132

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