Triethylamine → HCID 24751933, Verbindung

HRID 252243

Reaktionsgleichung

Reaktionsgleichung von HRID 252243
[N-]=C=O.[C:4]1([CH3:17])[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]([NH2:16])=[O:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Cl.N[C:20]1[S:21][C:22]([Br:25])=[CH:23][N:24]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:25][C:22]1[S:21][C:20]([NH:16][C:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([CH3:17])=[CH:9][CH:8]=2)(=[O:11])=[O:12])=[O:15])=[N:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 221703925-Bromo-1,3-thiazol-2-amine--hydrogen chloride (1/1)HCID 86616716Toluene-4-sulfonylurea isocyanate

Produkt 1

HCID 24751933HCID 24751933, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of toluene-4-sulfonylurea isocyanate (2.6 g, 13 mmol) in CH2Cl2 (10 ml) was added slowly to a mixture containing 2-amino-5-bromothiazole hydrochloride (3.4 g, 13 mmol) and triethylamine (5.4 ml, 39 mmol) in CH2Cl2 (60 ml) under an argon atmosphere and stirred overnight at rt. The reaction mixture was concentrated under reduce pressure, diluted with ethyl acetate and washed with NaHCO3 (half sat. 3×), 5% KHSO4/10% K2SO4, water, NaCl sat., dried (MgSO4.2H2O), filtered and concentrated under reduced pressure. Recrystallization from MeOH/water yielded a beige solid: 2.8 g (58%), MS: m/e 376.1 (MH+).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with NaHCO3 (half sat. 3×), 5% KHSO4/10% K2SO4, water, NaCl sat.
  4. dry with materialdried (MgSO4.2H2O)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization from MeOH/water
  8. customyielded a beige solid

Quellen und Nachweise

ORD-Eintrag
ord-de66dd01d4764801b519b2e2fd4230d7
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868030B2

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