Triethylamine → HCID 178420440, compound

HRID 484811Notes

Reaction equation

HRID 484811 reaction equation
[NH:1]1[C:5]([SH:6])=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[CH:14](Br)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[CH:14]([S:6][C:5]1[NH:4][N:3]=[N:2][N:1]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 236603BromodiphenylmethaneHCID 178527994HCID 178527994, compound

Product 1

HCID 178420440HCID 178420440, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1H-tetrazole-5-thiol (27.5 g) and triethylamine (59.9 g) in tetrahydrofuran (550 ml) was added benzhydryl bromide (66.6 g) and then the mixture was refluxed with stirring for 6.5 hours. After the addition of water and ethyl acetate to the reaction mixture, the pH was adjusted to 9.0 with 2N aqueous solution of sodium hydroxide. The aqueous layer was separated and washed with ethyl acetate. After the addition of ethyl acetate to the washed aqueous layer, the mixture was adjusted to pH 2.0 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated. The residue was pulverized in a mixture of isopropyl ether and n-hexane, collected by filtration, washed with a mixture of isopropyl ether and n-hexane and then dried to give 5-benzhydrylthio-1H-tetrazole (29.62 g), mp 132° to 134° C.

Workup

  1. temperaturethe mixture was refluxed
  2. customThe aqueous layer was separated
  3. washwashed with ethyl acetate
  4. additionAfter the addition of ethyl acetate to the washed aqueous layer
  5. customThe ethyl acetate layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. additionThe residue was pulverized in a mixture of isopropyl ether and n-hexane
  10. filtrationcollected by filtration
  11. washwashed with a mixture of isopropyl ether and n-hexane
  12. customdried

Sources & evidence

ORD record
ord-887538ce48bb45d098eacf955d69adae
Source dataset
uspto-grants-1985_08
Patent number
US04533738

Reaction notes

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