1,3-Di-Boc-2-methylisothiourea → HCID 86646935, Verbindung

HRID 1929340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929340
CS/[C:3](/[NH:12][C:13](=O)OC(C)(C)C)=[N:4]\[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[Cl:20][C:21]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:22]=1[CH2:23][O:24][C:25]1[CH:26]=[C:27]([NH2:32])C(N)=[CH:29][CH:30]=1>CO.C(O)(=O)C>[Cl:20][C:21]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:22]=1[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:13]2[N:12]=[C:3]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[NH:32][C:27]=2[CH:26]=1

Komponenten

5

Edukt 2

HCID 63760081,3-Di-Boc-2-methylisothioureaHCID 68511467HCID 68511467, Verbindung

Produkt 1

HCID 86646935HCID 86646935, VerbindungAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

add 615 mg of bis(1,1-dimethylethyl) [(Z)-(methylsulphanyl)methylylidene]biscarbamate to a solution of 600 mg of 4-[(2,6-dichlorobenzyl)oxy]benzene-1,2-diamine in a mixture of 30 cm3 of methanol and 127 mg of pure acetic acid. The mixture is refluxed for about 3 hours then concentrated under reduced pressure (0.2 kPa). The residue is taken up in 20 cm3 of a saturated aqueous solution of potassium carbonate and the mixture is extracted three times with 100 cm3 of dichloromethane. The combined organic phases are dried over magnesium sulphate, then filtered and evaporated under reduced pressure. After purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (98/2 by volume)], we obtain 586 mg of 1,1-dimethylethyl {6-[(2,6-dichlorobenzyl)oxy]-1H-benzimidazol-2-yl}carbamate in the form of an orange resin, which has the following characteristics:

Aufarbeitung

  1. temperatureThe mixture is refluxed for about 3 hours
  2. concentrationthen concentrated under reduced pressure (0.2 kPa)
  3. extractionthe mixture is extracted three times with 100 cm3 of dichloromethane
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customAfter purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (98/2 by volume)], we

Quellen und Nachweise

ORD-Eintrag
ord-32f46420833d4d768ba7cd58eb7cf23b
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188078B2

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