Toluene → S-(1-Phenyl-5-tetrazolyl) chlorothioformate

HRID 1085051

反応式

HRID 1085051 の反応式
[C:1]([Cl:4])(Cl)=[O:2].C1(C)C=CC=CC=1.C(N(CC)CC)C.[C:19]1([N:25]2[C:29]([SH:30])=[N:28][N:27]=[N:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[Cl:4][C:1]([S:30][C:29]1[N:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:26]=[N:27][N:28]=1)=[O:2]

参加物

6

反応物 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 1785279861-phenyltetrazole-5-thiol

生成物 1

HCID 86028543S-(1-Phenyl-5-tetrazolyl) chlorothioformate収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

A 20% phosgene solution in toluene (14.4 ml, 25.2 mmole) was added to a mixture of triethylamine (2.58 ml, 18.5 mmol) and 1-phenyl-1H-tetrazol-5-thiol (3.00 g, 16.8 mmole) in THF (15 ml) at 5° C. over 10 min. The reaction mixture was stirred for an hour at 5° C. and filtered. The filtrate obtained was evaporated and the residue washed thoroughly with ethyl ether. It was then recrystallized by dissolving in THF and precipitating with ethyl ether to give white crystal (2.92 g, 72%) m.p. 112°-114° C. IR (Film) 1718, 1645, 1590, 1490 and 1395 cm-1. 1H-NMR (CDCl3) δ7.52 (s, aromatic H).

後処理

  1. filtrationfiltered
  2. customThe filtrate obtained
  3. customwas evaporated
  4. washthe residue washed thoroughly with ethyl ether
  5. customIt was then recrystallized
  6. dissolutionby dissolving in THF
  7. customprecipitating with ethyl ether

出典と根拠

ORDレコード
ord-1303abd955924b758a34f64d6d910e9e
出典データセット
uspto-grants-1991_04
特許番号
US05008245

関連ノート

読み込み中…