Azido(trimethyl)stannane → HCID 178418841、化合物

HRID 11125

反応式

HRID 11125 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:27][CH2:28][C:29]#[N:30])[C:10]=2[CH:9]=1.[N:31]([Sn](C)(C)C)=[N+:32]=[N-:33]>C1(C)C=CC=CC=1.CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:27][CH2:28][C:29]3[NH:33][N:32]=[N:31][N:30]=3)[C:10]=2[CH:9]=1

参加物

6

反応物 2

HCID 5104973Azido(trimethyl)stannane2 回HCID 248846973-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)propanenitrile

生成物 1

HCID 178418841HCID 178418841、化合物収率 72.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21735183Dimethylformamide toluene溶媒

実験手順

To a solution of nitrile (238) (0.68 g, 1.63 mmol) prepared as described in example 98 in toluene/dimethylformamide (5:1, 120 mL) was added azidotrimethyl tin (0.67 g, 3.26 mmol). The resulting solution was heated at reflux for 24 hours before a further portion of azidotrimethyl tin (0.34 g, 1.63 mmol) was added. After a further 24 hours at reflux the reaction was diluted with water and extraction with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetatelhexane (3:1) to ethyl acetate/methanol (9:1), followed by crystallization from ethyl acetate/hexane, gave tetrazole (272) (0.54 g, 72%) as an orange powder, mp 230–234° C. (dec). 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.37 (br s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.61 (s, 1H), 7.56 (m, 1H), 7.48 (m, 4H), 7.10 (dd, J=8.8, 2.4 Hz, 1H), 4.82 (t, J=6.9 Hz, 2H), 3.32 (obscured t, J=6.9 Hz, 2H). Found: C, 52.69; H, 4.05; N, 15.91. C23H15ClN6O3.31/2H2O requires: C, 52.93; H, 4.25; N, 16.09.

後処理

  1. temperatureThe resulting solution was heated
  2. additionwas added
  3. temperatureAfter a further 24 hours at reflux the reaction
  4. customThe organic phase was dried
  5. customthe drying agent was removed
  6. concentrationthe solution was concentrated to dryness
  7. customChromatography on silica eluting with ethyl acetatelhexane (3:1) to ethyl acetate/methanol (9:1), followed by crystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-48da5ed2f8704646a3a54504d181f110
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

関連ノート

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