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

HRID 1170900노트

반응식

HRID 1170900 반응식
[C:1]([CH:3]([NH:9][CH:10]=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>[NH2:2][C:1]1[S:21][CH:10]=[N:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

6

반응물 2

HCID 87949Lawesson's reagentHCID 12562418Ethyl 2-cyano-2-formamidoacetate

생성물 1

HCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate수율 37.9%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 10340Sodium Carbonate용매

실험 절차

A solution of ethyl 2-cyano-2-formamidoacetate (480 mg, 3.07 mmol) and Lawesson's reagent (746 mg, 1.84 mmol) in toluene (5 mL) was heated up to 80° C. for overnight. The reaction was then diluted with sodium carbonate aqueous solution (20 mL) and methylene chloride (50 mL). Organic phase was washed with brine (20 mL), dried over sodium sulfate and concentrated. Purified with silica gel chromatography to give a solid material of ethyl 5-aminothiazole-4-carboxylate (120 mg). 1H NMR (400 MHz, CDCl3) δ 7.86 (s, 1H), 5.98 (s, br, 2H), 4.38 (q, 2H), 1.41 (t, 3H). MS m/z 173.2 (M+H)+.

후처리

  1. washOrganic phase was washed with brine (20 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customPurified with silica gel chromatography

출처 및 근거

ORD 기록
ord-9610a3078db14622a095263622674a8f
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829572B2

반응 노트

불러오는 중…