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

HRID 42792

反応式

HRID 42792 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-494ac4085b1b412d9895b560863ddcf1
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

関連ノート

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