Water → HCID 178453669, compound

HRID 1395788Notes

Reaction equation

HRID 1395788 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:9]([SH:10])=[N:8][N:7]=[N:6]1.[C:11]([O:15][C:16](N=[N+]=[N-])=[O:17])([CH3:14])([CH3:13])[CH3:12].O.O1CCOCC1>C(N(CC)CC)C>[C:11]([O:15][C:16]([NH:2][CH2:3][CH2:4][N:5]1[C:9]([SH:10])=[N:8][N:7]=[N:6]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 178479232HCID 178479232, compound

Product 1

HCID 178453669HCID 178453669, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 1-(2-aminoethyl)-1H-tetrazole-5-thiol hydrochloride (1.82 g.), t-butoxycarbonylazide (2.86 g.), water (20 ml.) and dioxane (20 ml.) was added triethylamine (6.0 g.), and the mixture was stirred at room temperature for one hour. After dioxane was removed therefrom under reduced pressure, the residue was adjusted to pH 7.5 to 8.0 with 5% aqueous solution of sodium bicarbonate and washed twice with ether. The resultant solution was adjusted to pH 1 with 5% hydrochloric acid and extracted three times with ethyl acetate (each 50 ml.). The extract was washed with an aqueous saturated solution of sodium chloride, dried over magnesium sulfate and then concentrated under reduced pressure to give 1-(2-t-butoxycarbonylaminoethyl)-1H-tetrazole-5-thiol (2.05 g.), m.p. 117° to 120° C. (dec.).

Workup

  1. customAfter dioxane was removed
  2. washwashed twice with ether
  3. extractionextracted three times with ethyl acetate (each 50 ml
  4. washThe extract was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93785a67ecab410294178f19fbe28741
Source dataset
uspto-grants-1980_05
Patent number
US04205166

Reaction notes

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