Ammonia → HCID 22063482, Verbindung

HRID 12093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12093
C(O[CH:9]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[C:19]([C:20](=[O:26])[CH:21](OCC)O)[C:11]=2[O:10]1)C1C=CC=CC=1.[CH:27]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1)([CH3:29])[CH3:28].[BH4-].[Na+].Cl.N>C(O)C.CC(C)=O.C(OCC)(=O)C.O>[CH2:20]([O:26][C:17]1[CH:18]=[C:19]([CH:20]([OH:26])[CH2:21][NH:40][C:37]([CH3:38])([CH3:39])[CH2:36][C:33]2[CH:32]=[CH:31][C:30]([CH:27]([CH3:29])[CH3:28])=[CH:35][CH:34]=2)[C:11]2[O:10][CH2:9][C:14](=[O:15])[NH:13][C:12]=2[CH:16]=1)[C:19]1[CH:11]=[CH:12][CH:16]=[CH:17][CH:18]=1

Komponenten

10

Edukt 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22063456HCID 22063456, VerbindungHCID 22063484HCID 22063484, Verbindung

Produkt 1

HCID 22063482HCID 22063482, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.18 g (6.1 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1.1 g (5.8 mmol) of 2-(4-isopropylphenyl)-1,1-dimethylethylamine are stirred in 40 mL ethanol at 50° C.-80° C. for one hour. After cooling to ambient temperature, 0.24 g (6.3 mmol) sodium borohydride is added. The mixture is stirred for one hour, diluted with 5 mL acetone, and stirred for a further 30 minutes. The reaction mixture is acidified with hydrochloric acid, combined with 100 mL water and 80 mL ethyl acetate, and made alkaline with ammonia. The organic phase is separated off, dried with sodium sulfate, and freed from solvent. The residue is dissolved in 20 mL ethyl acetate and 10 mL water, acidified with concentrated hydrochloric acid and diluted with diethyl ether. After the addition of a crystallization aid, the solid precipitate is suction filtered and washed. White solid. Yield: 1.7 g (52%, hydrochloride); melting point: 220° C.-222° C.

Aufarbeitung

  1. stirringstirred for a further 30 minutes
  2. customThe organic phase is separated off
  3. dry with materialdried with sodium sulfate
  4. dissolutionThe residue is dissolved in 20 mL ethyl acetate
  5. additiondiluted with diethyl ether
  6. additionAfter the addition of a crystallization aid
  7. filtrationfiltered
  8. washwashed

Quellen und Nachweise

ORD-Eintrag
ord-f142153d51594f39b957e0c4213d6559
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727984B2

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