Formaldehyde → 5-(1-Pyrrolidinylmethyl)-1-[4-(trifluoromethyl)phenyl]-1H-tetrazole

HRID 517753노트

반응식

HRID 517753 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]=O.C[Si]([N:12]=[N+:13]=[N-:14])(C)C.[F:15][C:16]([F:26])([F:25])[C:17]1[CH:22]=[CH:21][C:20]([N+:23]#[C-:24])=[CH:19][CH:18]=1>CO>[N:1]1([CH2:6][C:24]2[N:23]([C:20]3[CH:19]=[CH:18][C:17]([C:16]([F:25])([F:26])[F:15])=[CH:22][CH:21]=3)[N:14]=[N:13][N:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 78378AzidotrimethylsilaneHCID 27594124-(Trifluoromethyl)phenyl isocyanide

생성물 1

HCID 866918835-(1-Pyrrolidinylmethyl)-1-[4-(trifluoromethyl)phenyl]-1H-tetrazole수율 86%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of pyrrolidine (0.074 mL, 0.90 mmol) and formaldehyde (37%, aqueous, 0.067 mL, 0.9 mmol) in methanol (4 mL) was stirred at room temperature for 1.5 h before adding trimethylsilyl azide (0.155 mL, 1.170 mmol) and 4-(trifluoromethyl)phenyl isocyanide (200 mg, 1.170 mmol, Fluorochem, Old Glossop, UK). After stirring for 2 days the solution was concentrated in vacuo. The resulting residue was purified using MDAP. Fractions containing product were combined and concentrated in vacuo. The resulting solid was redissolved in MeOH and passed through a 5 g NH2 ion exchange column to yield the title compound as a solid (230 mg).

후처리

  1. concentrationwas concentrated in vacuo
  2. customThe resulting residue was purified
  3. additionFractions containing product
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting solid was redissolved in MeOH

출처 및 근거

ORD 기록
ord-d299a41c73a3454592099efa1dc0145c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115132B2

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