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Dichloromethane → Ethyl 2-((dimethylamino)methyl)thiazole-4-carboxylate

HRID 872671
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HRID 872671 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:11]Cl)[S:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:20][NH:21][CH3:22].C(Cl)Cl>CN(C=O)C>[CH3:20][N:21]([CH2:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=1)[CH3:22]
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참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 24715135Ethyl 2-(chloromethyl)-1,3-thiazole-4-carboxylate

생성물 1

HCID 2039211Ethyl 2-((dimethylamino)methyl)thiazole-4-carboxylate수율 34.2%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

실험 절차

2-Chloromethyl-thiazole-4-carboxylic acid ethyl ester (500 mg, 2.431 mmol) and potassium carbonate (504 mg, 3.65 mmol) were dissolved in dry DMF. Dimethylamine hydrochloride (218 mg, 2.67 mmol) in dry DMF was added slowly to the reaction mixture and stirred at RT over three nights. DCM was added and the mixture was washed with concentrated NaHCO3 and water. Organic phase was evaporated to dryness and the product was purified by Flash-chromatography. Yield 34.2%. 1H-NMR (400 MHz; CDCl3): δ 1.41 (t, 3H), 2.49 (s, 6H), 3.99 (s, 2H) 4.43 (q, 2H), 8.20 (s, 1H).

후처리

  1. washthe mixture was washed with concentrated NaHCO3 and water
  2. customOrganic phase was evaporated to dryness
  3. customthe product was purified by Flash-chromatography

출처 및 근거

ORD 기록
ord-24a52f0a45694d8e954b1aa47589d923
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975254B2

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