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Triethylamine → 2-Ethyl-4-methoxybenzothiazole-7-carboxylic acid (3,5-dimethylisoxazol-4-yl)amide

HRID 427295
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HRID 427295 반응식
[CH2:1]([C:3]1[S:4][C:5]2[C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[C:6]=2[N:7]=1)[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:23][C:24]1[C:28]([NH2:29])=[C:27]([CH3:30])[O:26][N:25]=1.C(N(CC)CC)C>ClCCl>[CH3:23][C:24]1[C:28]([NH:29][C:12]([C:11]2[C:5]3[S:4][C:3]([CH2:1][CH3:2])=[N:7][C:6]=3[C:8]([O:15][CH3:16])=[CH:9][CH:10]=2)=[O:14])=[C:27]([CH3:30])[O:26][N:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1820404-Amino-3,5-dimethylisoxazoleHCID 183570002-Ethyl-4-methoxybenzothiazole-7-carboxylic acid

생성물 1

HCID 98587562-Ethyl-4-methoxybenzothiazole-7-carboxylic acid (3,5-dimethylisoxazol-4-yl)amide수율 11.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

To a suspension of 2-ethyl-4-methoxybenzothiazole-7-carboxylic acid (0.1 g) in dichloromethane (10 ml) was added oxalyl chloride (0.08 ml) and dimethylformanide (1 drop). The reaction was stirred at room temperature for 16 hrs, and then the solvent was removed in vacuo to yield a brown solid residue. This was taken up in dichloromethane is (30 ml) and 3,5-dimethylisoxazol-4-amine (0.05 g) was added followed by triethylamine (0.15 ml) and the reaction stirred at room temperature for 16 hrs. The solvent was removed in vacuo and the product purified by flash chromatography (eluent ethyl acetate) to yield the title compound as an off-white solid (0.016 g). TLC Rf 0.38 (ethyl acetate); Mpt 85-87° C.

후처리

  1. customthe solvent was removed in vacuo
  2. customto yield a brown solid residue
  3. additionwas added
  4. stirringthe reaction stirred at room temperature for 16 hrs
  5. customThe solvent was removed in vacuo
  6. customthe product purified by flash chromatography (eluent ethyl acetate)

출처 및 근거

ORD 기록
ord-87f7f21d60a34c1ea673d11d379c6062
출처 데이터셋
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06313116B1

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