Lawesson's reagent → Ethyl 5-amino-1,3-thiazole-4-carboxylate

HRID 1674708노트

반응식

HRID 1674708 반응식
[CH:1]([NH:3][C@H:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]#[N:6])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1C=CC=CC=1>[NH2:6][C:5]1[S:21][CH:1]=[N:3][C:4]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 86619658Ethyl N-formyl-3-nitriloalaninate

생성물 1

HCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Ethyl N-formyl-3-nitriloalaninate (11.22 g, 71.86 mmol) is dissolved in anhydrous benzene (220 mL). Following the addition of Lawesson's reagent (14.53 g, 35.93 mmol), the suspension is refluxed for 24 h. Most of the solvent is removed in vacuo, and the viscous red residue is absorbed on silica gel and loaded to a silica gel column (elution solvent: EtOAc:hexanes=50:50). The title compound is obtained as yellow solids. 1H NMR (400 MHz, CDCl3) 7.87 (1H, s), 7.26 (1H, s), 6.01 (2H, broad s), 4.38 (2H, q), 1.41 (3H, t).

후처리

  1. temperaturethe suspension is refluxed for 24 h
  2. customMost of the solvent is removed in vacuo
  3. customthe viscous red residue is absorbed on silica gel
  4. washloaded to a silica gel column (elution solvent: EtOAc:hexanes=50:50)

출처 및 근거

ORD 기록
ord-50dbc6b5bfcb457abdce22272d52d9a6
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003656B2

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