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Hydrochloric Acid → HCID 20033680, Verbindung

HRID 231682
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 231682
[CH3:1][N:2]([CH3:24])[C:3]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[S:19][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)=O.Cl.[CH2:26](NCCC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1)[CH3:27].CN(C)CCCC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1.CN(C)CCCCC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1>O1CCCC1>[CH3:1][N:2]([CH3:24])[CH:3]([CH2:26][CH3:27])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[S:19][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 20033708HCID 20033708, VerbindungHCID 20033710HCID 20033710, VerbindungHCID 20033716HCID 20033716, VerbindungHCID 20033728HCID 20033728, Verbindung

Produkt 1

HCID 20033680HCID 20033680, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

5-(4-dimethylcarbamoylmethylphenylsulfonyl)thiophene-2-sulfonamide (1.35 g) was dissolved in 30 ml of tetrahydrofuran under a nitrogen atmosphere. Borane tetrahydrofuran complex (8 ml of 1 molar solution) was added and the mixture was stirred at room temperature for 3 hours. Hydrochloric acid (20 ml of 6N) was then added cautiously and the mixture was heated on a steam bath, boiling off tetrahydrofuran. The acidic solution was cooled to room temperature and extracted with chloroform. The aqueous phase was separated and its pH adjusted to pH 8.5 before extracting it with ethyl acetate. The ethyl acetate phase was dried over sodium sulfate and concentrated under vacuum to give a residue of an oily solid. This was chromatographed on silica gel to give a pure product, m.p. 169°-172° C. N.M.R. (DMSO, d6) δ: 2.17 (6H, s), 2.50 (2H, T, J=6 Hz), 2.82 (2H, T, J=6 Hz), 7.55 (2H, d, J=9 Hz), 7.60 (1H, d, J=4 Hz), 7.87 (1H, d, J=4 Hz), 7.94 (2H, d, J=9 Hz), 8.04 (2H, broad s). Anal Calc'd for C14H18N2O4S3 : C, 44.90; H, 4.84; N, 7.48. Found: C, 44.54; H, 4.89; N, 7.60. The following compounds where also made by similar procedures: 5-[4-(2-ethylaminoethyl)phenylsulfonyl]thiophene-2-sulfonamide (m.p. 174-177). 5-[4-(3-methylaminopropyl)phenylsulfonyl]thiophene-2-sulfonmide (m.p. 178°-179.5° C.), 5-[4-(3-dimethylaminopropyl)phenylsulfonyl]thiophene-2-sulfonamide (m.p. 163°-164.5° C.), and 5-[4-(4-dimethylaminobutyl)phenylsulfonyl]thiophene-2-sulfonamide (m.p. 186°-189° C.).

Aufarbeitung

  1. additionBorane tetrahydrofuran complex (8 ml of 1 molar solution) was added
  2. temperaturethe mixture was heated on a steam bath
  3. temperatureThe acidic solution was cooled to room temperature
  4. extractionextracted with chloroform
  5. customThe aqueous phase was separated
  6. extractionbefore extracting it with ethyl acetate
  7. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customto give a residue of an oily solid
  10. customThis was chromatographed on silica gel
  11. customto give a pure product, m.p. 169°-172° C

Quellen und Nachweise

ORD-Eintrag
ord-cafc0eb136e247d58e5a51f3ab7293c1
Quelldatensatz
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04847289

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