Triethylamine → HCID 178458014, compound

HRID 543844Notes

Reaction equation

HRID 543844 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([N:6]1[C:10]([SH:11])=[N:9][N:8]=[N:7]1)[CH3:5].C(N(CC)CC)C.[C:19]([O:23][C:24](ON=C(C1C=CC=CC=1)C#N)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCOCC1>[C:19]([O:23][C:24]([NH:2][CH2:3][CH:4]([N:6]1[C:10]([SH:11])=[N:9][N:8]=[N:7]1)[CH3:5])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 178458047HCID 178458047, compound

Product 1

HCID 178458014HCID 178458014, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-[1-(aminomethyl)ethyl-1H-tetrazole-5-thiol hydrochloride (17 g) and triethylamine (19.33 g) in 50% aqueous dioxane (80 ml) was added a solution of 2-t-butoxycarbonyloxyimino-2-phenylacetonitrile (21.4 g) in dioxane (50 ml) under cooling in an ice bath. The mixture was stirred for 1.5 hours at ambient temperature and concentrated to third volume. The aqueous solution was washed with diethyl ether and the washings were reextracted with aqueous solution of potassium carbonate. The two aqueous solutions were combined, washed with diethyl ether and mixed with ethyl acetate. The mixture was acidified with 10% hydrochloric acid and the organic layer was separated out. The solution was dried over magnesium sulfate and evaporated to dryness. The residue was triturated with n-hexane to give 1-[1-{(N-t-butoxycarbonylamino)methyl}ethyl]-1H-tetrazole-5-thiol (19.15 g), mp 156° to 158° C.

Workup

  1. temperatureunder cooling in an ice bath
  2. concentrationconcentrated to third volume
  3. washThe aqueous solution was washed with diethyl ether
  4. washwashed with diethyl ether
  5. additionmixed with ethyl acetate
  6. customthe organic layer was separated out
  7. dry with materialThe solution was dried over magnesium sulfate
  8. customevaporated to dryness
  9. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-b6662768f53c473c9b75436db36ded80
Source dataset
uspto-grants-1984_05
Patent number
US04447429

Reaction notes

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