Sulfuryl chloride → 4-Bromoacetyl-2-geranyloxy-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 36570

Reaktionsgleichung

Reaktionsgleichung von HRID 36570
[Br:1][CH2:2][C:3]([N:5]1[CH2:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8][CH2:7][CH2:6]1)=[O:4].S(Cl)(Cl)(=O)=O.[CH3:21][C:22](=[CH:24][CH2:25][CH2:26]/[C:27](=[CH:29]/[CH2:30][OH:31])/[CH3:28])[CH3:23]>[Cl-].[Zn+2].[Cl-]>[Br:1][CH2:2][C:3]([N:5]1[CH2:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8][CH:7]([O:31][CH2:30]/[CH:29]=[C:27](/[CH2:26][CH2:25][CH:24]=[C:22]([CH3:23])[CH3:21])\[CH3:28])[CH2:6]1)=[O:4]

Komponenten

5

Edukt 3

HCID 24648Sulfuryl chlorideHCID 637566GeraniolHCID 152916574-Bromoacetyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

Produkt 1

HCID 152916604-Bromoacetyl-2-geranyloxy-2,3,4,5-tetrahydro-1,4-benzothiazepineAusbeute 24,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Versuchsvorschrift

The above-mentioned 4-bromoacetyl-2,3,4,5-tetrahydro-1,4-benzothiazepine (2.5 g) and sulfuryl chloride (1.5 g) were reacted in the same manner as in Experimental Example 7 to give 4-bromoacetyl-2-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepmne (1.4 g). This compound (0.30 g), geraniol (0.30 g) and zinc chloride (0.26 g) were reacted in the same manner as in Experimental Example 9 to give 4-bromoacetyl-2-geranyloxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (0.21 g). Then, this compound (0.21 g), 4-benzyl piperidine (O.11 g) and potassium carbonate (0.13 g) were reacted in the same manner as in Experimental Example 6 to give 4-[1-(4-benzyl) piperidinyl]acetyl-2-geranyloxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (0.26 g).

Aufarbeitung

  1. customto give 4-bromoacetyl-2-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepmne (1.4 g)

Quellen und Nachweise

ORD-Eintrag
ord-4a7cf56ef5fc412889de65a617252d8f
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416066

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