Triethylamine → Methyl 5-(4-fluorophenyl)-1,2,3-thiadiazole-4-carboxylate

HRID 30626

반응식

HRID 30626 반응식
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=O)=[CH:4][CH:3]=1.C1(C)C=CC([S:21]([N:24]=[N+:25]=[N-])(=O)=O)=CC=1.C(N(CC)CC)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>O1CCCC1.O.C(#N)C>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]2[S:21][N:24]=[N:25][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 87949Lawesson's reagentHCID 579425Methyl 4-fluorobenzoylacetate

생성물 1

HCID 69207857Methyl 5-(4-fluorophenyl)-1,2,3-thiadiazole-4-carboxylate수율 41%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A mixture of methyl 4-fluorobenzoylacetate (3.92 g), p-toluenesulfonyl azide (4.00 g), triethylamine (2.02 g) and acetonitrile (30 ml) was stirred at 0° C. for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give a yellow oil. The Lawesson's reagent (8.10 g) and tetrahydrofuran (50 ml) were added to this yellow oil and the mixture was heated under reflux for 16 hrs. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography to give methyl 5-(4-fluorophenyl)-1,2,3-thiadiazole-4-carboxylate (1.95 g, yield 41%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 16 hrs
  8. concentrationThe reaction mixture was concentrated
  9. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-51cc9f5cc6e04895a44af5f42d9f0f93
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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