Nitrogen → Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

HRID 42792

반응식

HRID 42792 반응식
N#N.[CH2:3]([O:5][C:6](=[O:10])[C:7]([NH2:9])=[S:8])[CH3:4].[Cl:11][CH2:12][C:13](=O)[CH2:14]Cl.CCOC(C)=O>C1(C)C=CC=CC=1>[CH2:3]([O:5][C:6]([C:7]1[S:8][CH:14]=[C:13]([CH2:12][Cl:11])[N:9]=1)=[O:10])[CH3:4]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 8857Ethyl AcetateHCID 107931,3-DichloroacetoneHCID 2733398Ethyl thiooxamate

생성물 1

HCID 10822129Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of amino-thioxo-acetic acid ethyl ester (2.50 g, 18.77 mmol) and 1,3-dichloro-propan-2-one (2.88 g, 21.59 mmol) in toluene (20.0 mL) was stirred for 2 h at reflux. EtOAc (20 mL) was added at rt and the mixture was washed with sat. aq. NaHCO3 (10 mL) followed by brine (20 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a light yellow oil. TLC:rf (4:1 hept-EA)=0.26. LC-MS-conditions 02: tR=0.89 min, [M+H]+=206.40.

후처리

  1. temperatureat reflux
  2. washthe mixture was washed with sat. aq. NaHCO3 (10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customPurification of the residue by FC (4:1 hept-EA)

출처 및 근거

ORD 기록
ord-494ac4085b1b412d9895b560863ddcf1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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