Hydrochloric Acid → 5-(3,5-Dimethyl-benzylcarbamoyl)-thiophene-3-carboxylic acid ethyl ester

HRID 1837614노트

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HRID 1837614 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:11]([OH:13])=O)[S:9][CH:10]=1)=[O:5])[CH3:2].CN(C)CCCN=C=NCC.Cl.[CH3:26][C:27]1[CH:28]=[C:29]([CH:32]=[C:33]([CH3:35])[CH:34]=1)[CH2:30][NH2:31]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:11](=[O:13])[NH:31][CH2:30][C:29]2[CH:32]=[C:33]([CH3:35])[CH:34]=[C:27]([CH3:26])[CH:28]=2)[S:9][CH:10]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27362413,5-DimethylbenzylamineHCID 202775414-(Ethoxycarbonyl)thiophene-2-carboxylic acid

생성물 1

HCID 695434975-(3,5-Dimethyl-benzylcarbamoyl)-thiophene-3-carboxylic acid ethyl ester수율 73.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

0.5 g 2-carboxy-thiophen-4-carboxylic acid ethyl ester (M. Janda, J. Srogl, M. Nemec, I. Stibor; Org. Prep. and Proced. Int. 3 (6) (1971) 295.) and 0.67 g N′-(3-dimethylaminopropyl)-N-ethylcarbodiimid×HCl are stirred in 50 mL DCM for 15 min. Then, 0.338 g 3,5-dimethylbenzylamin are added and the mixture is stirred overnight. The solution is extracted with 2N HCl and water, then evaporated. The residue is titurated with isohexan, and the resulting crystals are filtrated and air-dried, yielding 0.58 g (73%) crude 5-(3,5-Dimethyl-benzylcarbamoyl)-thiophene-3-carboxylic acid ethyl ester (7b). This ester in converted to title compound by reaction with hydroxylamine hydrochloride in a manner similar to that described for the conversion of 4b into 4a in example 4. After chromatography (silica, ethylacetate), thiophene-2,4-dicarboxylic acid 2-(3,5-dimethyl-benzylamide) 4-hydroxyamide (7a) is obtained as crystals; 44 mg, 9%, mp: 181° C. (decomp.).

후처리

  1. extractionThe solution is extracted with 2N HCl and water
  2. customevaporated
  3. filtrationthe resulting crystals are filtrated
  4. customair-dried

출처 및 근거

ORD 기록
ord-84921da024c8432f9171f14d453d8926
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784173B2

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