Trimethyltin chloride → 5-(2,4-dibenzyloxyphenyl)-2H-tetrazole hydrate

HRID 322852

反応式

HRID 322852 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Sn](Cl)(C)C.[N-:30]=[N+:31]=[N-:32].[Na+]>C1(C)C=CC=CC=1>[OH2:8].[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:10]=1[C:11]1[N:30]=[N:31][NH:32][N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 14016Trimethyltin chlorideHCID 33557Sodium AzideHCID 103136042,4-Dibenzyloxybenzonitrile

生成物 1

HCID 220101945-(2,4-dibenzyloxyphenyl)-2H-tetrazole hydrate収率 137.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A suspension of 2,4-dibenzyloxybenzonitrile (1.89 g) in dry toluene (200 mL) is treated with trimethyltin chloride (6 g) and sodium azide (2 g). The mixture is stirred at reflux for 3 days, evaporated and the residue partitioned between dichloromethane (250 mL) and water (165 mL). The organic phase is washed with brine (165 mL), dried over magnesium sulphate and evaporated. The resulting semi-solid is triturated with ether (30 mL) and the solid washed with pentane and crystallised from a mixture of ethyl acetate and pentane to give 5-(2,4-dibenzyloxyphenyl)-2H-tetrazole hydrate (1.55 g) as a white solid, m.p. 178-179° C. [Elemental analysis:- C,69.7; H,5.02; N,15.4%. Calculated for C21H18N4O2.0.2H2O:- C,68.68; H,5.12; N,15.48%].

後処理

  1. temperatureat reflux for 3 days
  2. customevaporated
  3. customthe residue partitioned between dichloromethane (250 mL) and water (165 mL)
  4. washThe organic phase is washed with brine (165 mL)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe resulting semi-solid is triturated with ether (30 mL)
  8. washthe solid washed with pentane
  9. customcrystallised from a mixture of ethyl acetate and pentane

出典と根拠

ORDレコード
ord-d9370944c7b84c908d9d9ac5d14634f6
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

関連ノート

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