Formamide → Methyl 4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

HRID 1051911ノート

反応式

HRID 1051911 の反応式
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH:15]([NH2:17])=O.Br[CH:19]1[C:24](=O)[CH2:23][CH2:22][CH2:21][CH:20]1[C:26]([O:28][CH3:29])=[O:27]>O1CCOCC1>[S:2]1[C:19]2[CH:20]([C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:22][CH2:23][C:24]=2[N:17]=[CH:15]1

参加物

5

反応物 3

HCID 713FormamideHCID 14817Phosphorus sulfide (P2S5)HCID 83646766HCID 83646766、化合物

生成物 1

HCID 90303216Methyl 4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

At 0° C., finely crushed P4S10 (9.35 g, 21.0 mmol) was added to a mixture of formamide (4.73 g, 105.0 mmol) in dioxane (28.5 mL). Subsequently, the mixture was stirred in a sealed vial at 100° C. for 1.5 h, cooled to RT and filtrated. The filtrate was added to a mixture of methyl 2-bromo-3-oxocyclohexanecarboxylate (2.06 g, 8.76 mmol) in dioxane (16.5 mL) and stirred in a sealed vial at 80° C. overnight. The mixture was quenched by the addition of aq. sat. NaHCO3 and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. Purification by means of CC (10-40% EtOAc/Hept) provided a yellow oil.

後処理

  1. temperaturecooled to RT
  2. filtrationfiltrated
  3. stirringstirred in a sealed vial at 80° C. overnight
  4. customThe mixture was quenched by the addition of aq. sat. NaHCO3
  5. extractionextracted with EtOAc
  6. washlayers were washed with brine
  7. dry with materialdried over MgSO4
  8. customPurification by means of CC (10-40% EtOAc/Hept)
  9. customprovided a yellow oil

出典と根拠

ORDレコード
ord-8be6ff8a724c4742808a0d1c8404842b
出典データセット
uspto-grants-2016_07
特許番号
US09388197B2

反応ノート

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