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

HRID 1085051Notes

Reaction equation

HRID 1085051 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1303abd955924b758a34f64d6d910e9e
Source dataset
uspto-grants-1991_04
Patent number
US05008245

Reaction notes

Loading…