Triethylamine → HCID 20216823, compound

HRID 236284Notes

Reaction equation

HRID 236284 reaction equation
[C:1](Cl)([Cl:3])=[S:2].[C:5]1([N:11]2[C:15]([SH:16])=[N:14][N:13]=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCN(CC)CC>C1COCC1>[Cl:3][C:1]([S:16][C:15]1[N:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:12]=[N:13][N:14]=1)=[S:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 20216823HCID 20216823, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of thiophosgene (1.29 g, 0.0112 mol) in THF (40 ml) at 5° C. was added a solution of 1-phenyl-1H-tetrazole-5-thiol (2.0 g, 0.0112 mol) and Et3N (1.94 ml, 0.0134 mol) in THF (30 ml). The mixture was stirred at 5° C. for 30 min and then at r.t. for 1 hr. 20 min. The precipitate was filtered and washed with THF. The filtrate was evaporated in vacuo. To the obtained residue was added ether and the insoluble material was filtered off. The filtrate was evaporated in vacuo to give a solid which was recrystallized from CHCl3 --hexane. 0.91 g of the compound was obtained. 27.6% yield. IR (Nujol): 1725, 1585 cm-1.

Workup

  1. waitat r.t. for 1 hr
  2. custom20 min
  3. filtrationThe precipitate was filtered
  4. washwashed with THF
  5. customThe filtrate was evaporated in vacuo
  6. additionTo the obtained residue was added ether
  7. filtrationthe insoluble material was filtered off
  8. customThe filtrate was evaporated in vacuo
  9. customto give a solid which
  10. customwas recrystallized from CHCl3

Sources & evidence

ORD record
ord-2db68c765ae74a37aa3f449a523abe3a
Source dataset
uspto-grants-1987_02
Patent number
US04643991

Reaction notes

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