Triethylamine → HCID 178453503, compound

HRID 1759648Notes

Reaction equation

HRID 1759648 reaction equation
[C:1]([O:5][C:6]([O:8]N=C(C1C=CC=CC=1)C#N)=O)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:20][CH2:21][CH2:22][CH2:23][N:24]1[C:28]([SH:29])=[N:27][N:26]=[N:25]1.C(N(CC)CC)C>O1CCOCC1.O>[C:1]([O:5][C:6]([NH:20][CH2:21][CH2:22][CH2:23][N:24]1[C:28]([SH:29])=[N:27][N:26]=[N:25]1)=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 178479216HCID 178479216, compound

Product 1

HCID 178453503HCID 178453503, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2-t-butoxycarbonyloxyimino-2-phenylacetonitrile (12.3 g) in dioxane (30 ml) was added under ice-cooling to a stirred solution of 1-(3-aminopropyl)-1H-tetrazole-5-thiol hydrochloride (9.78 g) and triethylamine (11.1 g) in a mixture of dioxane (25 ml) and water (25 ml), and then the resulting mixture was stirred for 1.75 hours at ambient temperature. Dioxane was distilled off and to the residue were added diethyl ether and a small amount of water. After shaking, the aqueous layer was separated and the organic layer was extracted twice with 10% potassium carbonate. The extracts combined with the separated aqueous layer were washed three times with diethyl ether, adjusted to pH 1 with hydrochloric acid and extracted with diethyl ether. The extract was washed with water, dried and evaporated in vacuo. The residual oil (10.92 g) was pulverized with diisopropyl ether to give 1-[3-(N-t-butoxycarbonylamino)propyl]-1H-tetrazole-5-thiol (9.6 g), mp. 75° to 77° C.

Workup

  1. distillationDioxane was distilled off and to the residue
  2. additionwere added diethyl ether
  3. stirringAfter shaking
  4. customthe aqueous layer was separated
  5. extractionthe organic layer was extracted twice with 10% potassium carbonate
  6. washwere washed three times with diethyl ether
  7. extractionextracted with diethyl ether
  8. washThe extract was washed with water
  9. customdried
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-9c9266fb1fb6465da0d2b9d836ad0f94
Source dataset
uspto-grants-1982_07
Patent number
US04341775

Reaction notes

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