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Hydrochloric Acid → Unii-IS4M82C29X

HRID 1421269
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1421269
[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[CH:12][CH:13]=[C:5]3[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)[CH:8]=[CH:9][CH:10]=2)[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.Cl>ClCCl.C1(C)C=CC=CC=1.C(OCC)(=O)C.C(OCC)(=O)C.O.O1CCCC1>[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[CH:12][CH:13]=[C:5]3[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH:8]=[CH:9][CH:10]=2)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 18706925HCID 18706925, Verbindung2×

Produkt 1

HCID 9903336Unii-IS4M82C29XAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 21584019Toluene ethylacetateLösungsmittel

Versuchsvorschrift

A solution of 1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (Compound 34) (0.77 g, 2.79 mmol) in 25 ml of dry dichloromethane was stirred under a nitrogen atmosphere and aluminium chloride (2.23 g, 16.7 mmol) was added in portions. When the addition was complete, ethanethiol (1.25 ml, 16.7 mmol) was added, and stirring was continued for half an hour. The mixture was cooled in an ice bath followed by the addition of tetrahydrofuran (15 ml), 6M hydrochloric acid (3 ml), water (50 ml) and ethyl acetate (100 ml). The organic phase was separated and evaporated to leave a residue which was chromatograped over silica gel with toluene/ethyl acetate (4:1) as eluent. The proper fractions were collected and evaporated, and the residue was triturated with a mixture of ether (2 ml) and petroleum ether (5 ml) to afford 0.32 g (44%) of the title compound. M.p. 104-05° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.41 (t, 3H), 3.22 (q, 2H), 6.98 (d, 2H), 7.29 (d, 1H), 7.67 (d, 2H), 7.69(d, 1H), 7.72(t, 1H), 8.05 (d, 1H), 8.10 (d, 1H), 9.68 (s, 1H). (Compound 52).

Aufarbeitung

  1. additionWhen the addition
  2. waitwas continued for half an hour
  3. temperatureThe mixture was cooled in an ice bath
  4. customThe organic phase was separated
  5. customevaporated
  6. customto leave a residue which
  7. customThe proper fractions were collected
  8. customevaporated
  9. customthe residue was triturated with a mixture of ether (2 ml) and petroleum ether (5 ml)

Quellen und Nachweise

ORD-Eintrag
ord-a374bcabcbc34a1ba1af58cf0c0f7be5
Quelldatensatz
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06075036

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