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

HRID 30626

反応式

HRID 30626 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-51cc9f5cc6e04895a44af5f42d9f0f93
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

関連ノート

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