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

HRID 1051954노트

반응식

HRID 1051954 반응식
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

참가 물질

5

반응물 3

HCID 713FormamideHCID 14817Phosphorus sulfide (P2S5)HCID 83646766HCID 83646766, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-263acd6711eb446e9db5559b644bf796
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388198B2

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