Hydrochloric Acid → 1-(tert.-Butylamino)-3-[(1-phenyl-5-tetrazolyl)oxy]-2-propanol Hydrochloride

HRID 1414021Notes

Reaction equation

HRID 1414021 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]=[N:7][N:6]=1.[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18].[ClH:22]>C1C=CC=CC=1>[ClH:22].[C:17]([NH:21][CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]=[N:7][N:6]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 123998231-(1-Phenyltetrazol-5-yloxy)-2,3-epoxypropane

Product 1

HCID 123998321-(tert.-Butylamino)-3-[(1-phenyl-5-tetrazolyl)oxy]-2-propanol Hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,3-Epoxy-1-[(1-phenyl-5-tetrazolyl)oxy]propane (43.7 g., 0.20 mole) was heated at the reflux temperature in 150 ml. of tert.-butylamine and 300 ml. of benzene for 9 hours. The solvents were evaporated in vacuo and the residual oil was dissolved in 100 ml. of EtOH and acidified with ethanolic HCl. Dilution with diethyl ether gave 44.8 g. of the hydrochloride of the product, m.p. 73°-82°. Recrystallization from i-PrOH-IPE gave 30.8 g., m.p. 152.5°-154.5° (corr.).

Workup

  1. customThe solvents were evaporated in vacuo
  2. dissolutionthe residual oil was dissolved in 100 ml
  3. customDilution with diethyl ether gave 44.8 g
  4. customRecrystallization from i-PrOH-IPE
  5. customgave 30.8 g

Sources & evidence

ORD record
ord-309d2e3ecaaf45b3be79ed90c38ad93a
Source dataset
uspto-grants-1981_02
Patent number
US04252815

Reaction notes

Loading…