Methyl chloroformate → N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide

HRID 1719582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719582
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][CH2:9][C:10](O)=[S:11])=[N:5][N:4]=[N:3]1.CN1[CH2:19][CH2:18][O:17][CH2:16]C1.ClC(OC)=O.CO[CH:27]1[CH2:32]CC[CH2:29][CH:28]1[NH2:33]>O.C(Cl)Cl>[CH3:16][O:17][CH:18]1[CH2:19][CH2:29][CH:28]([NH:33][C:10](=[S:11])[CH2:9][CH2:8][CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)[CH2:27][CH2:32]1

Komponenten

7

Edukt 4

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 222508792-Methoxycyclohexan-1-amineHCID 178482013HCID 178482013, Verbindung

Produkt 1

HCID 53790851N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatograpy (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263.

Aufarbeitung

  1. customat 10°-20° C.
  2. temperaturecooling
  3. stirringthe mixture is stirred at the same temperature for 4 hours
  4. additionis added to the reaction mixture
  5. customThe organic layer is separated
  6. washwashed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order
  7. dry with materialdried over sodium sulfate
  8. filtrationInorganic materials are filtered off
  9. concentrationthe mother liquor is concentrated
  10. washThe resulting residue is subjected to column chromatograpy (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-32882580c07342d5aa5c25e8b5339e00
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04540703

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