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

HRID 1085051

반응식

HRID 1085051 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1303abd955924b758a34f64d6d910e9e
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05008245

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