Dimethyl-1,3-thiazole-5-carboxylic acid → HCID 19782022, 화합물

HRID 257855노트

반응식

HRID 257855 반응식
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.[CH2:11]([O:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][C:19]2[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1)[CH3:12]>C(Cl)(Cl)Cl>[CH2:11]([O:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][C:19]2[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:8]([C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=3[CH3:7])=[O:10])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1)[CH3:12]

참가 물질

4

반응물 2

HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 196273204-(4-Ethoxyphenoxy)benzenemethanamine

생성물 1

HCID 19782022HCID 19782022, 화합물수율 45%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To a stirred mixture of 2,4-dimethyl-1,3-thiazole-5-carboxylic acid (156 mg, 0.993 mM) and chloroform (20 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimde (190 mg, 0.393 mM) at 0°-10° C., and the mixture was stirred for 30 min at the same temperature. To this was added a solution (10 ml) of 4-(4-ethoxyphenoxy)benzylamine (242 mg, 0.993 mM) in chloroform at 0°-10° C., and the mixture was stirred for 12 h at the room temperature. The mixture was poured into ice water, and the mixture was extracted with chloroform. The extract was washed with saturated ammonium chloride solution and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give N-[4-(4-ethoxyphenoxy)benzyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide (171 mg, 45%) as colorless crystals, m.p. 99°-101° C.

후처리

  1. additionwas added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimde (190 mg, 0.393 mM) at 0°-10° C.
  2. stirringthe mixture was stirred for 12 h at the room temperature
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with saturated ammonium chloride solution and brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed over silica gel

출처 및 근거

ORD 기록
ord-8dcceae3076841b6b364a8dbcc6bbe61
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264448

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