Triethylamine → Ethyl N-butyl-N-(4-methyl-2-oxazolyl)-carbamate

HRID 46758

Reaktionsgleichung

Reaktionsgleichung von HRID 46758
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH2:7]([NH:11][C:12]1[O:13][CH:14]=[C:15]([CH3:17])[N:16]=1)[CH2:8][CH2:9][CH3:10].C(N(CC)CC)C>CCOCC>[CH2:7]([N:11]([C:12]1[O:13][CH:14]=[C:15]([CH3:17])[N:16]=1)[C:2](=[O:3])[O:4][CH2:5][CH3:6])[CH2:8][CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 122952262-Oxazolamine, N-butyl-4-methyl-

Produkt 1

HCID 23468959Ethyl N-butyl-N-(4-methyl-2-oxazolyl)-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Ethyl chloroformate (10.5 ml, 0.11 mol) was added dropwise over 20 minutes to a stirred solution of 2-butylamino-4-methyl oxazole (15.4 g, 0.10 mol) and triethylamine (15.3 ml, 0.11 mol) in dry ether (100 ml) cooling to 5°-10° C. The mixture was stirred for a further 2 hours at ambient temperature, the white solid was filtered off and the filtrate evaporated under vacuum to a pale oil (22.4 g) NMR (CCl4) 6.3 δ (oxazole 5-H). This 3-acylated compound was dissolved in xylene and the solution was heated under reflux for 2 hours, cooled, washed with dilute HCl, saturated NaCl solution, dilute Na2CO3 and NaCl solution again, dried and evaporated. The residue was distilled under vacuum, b.p. 85°-90° C./0.6 mm NMR (CCl4) 7.12 δ (oxazole 5-H).

Aufarbeitung

  1. temperaturecooling to 5°-10° C
  2. filtrationthe white solid was filtered off
  3. customthe filtrate evaporated under vacuum to a pale oil (22.4 g) NMR (CCl4) 6.3 δ (oxazole 5-H)
  4. dissolutionThis 3-acylated compound was dissolved in xylene
  5. temperaturethe solution was heated
  6. temperatureunder reflux for 2 hours
  7. temperaturecooled
  8. washwashed with dilute HCl, saturated NaCl solution, dilute Na2CO3 and NaCl solution again
  9. customdried
  10. customevaporated
  11. distillationThe residue was distilled under vacuum, b.p. 85°-90° C./0.6 mm NMR (CCl4) 7.12

Quellen und Nachweise

ORD-Eintrag
ord-709efc0ae90d46f48803521f1b89afcb
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175131

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