Acetic Anhydride → N-(7-bromobenzo[d]thiazol-2-yl)acetamide

HRID 2077515

Reaktionsgleichung

Reaktionsgleichung von HRID 2077515
[Br:1][C:2]1[C:10]2[S:9][C:8]([NH2:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.BrC1C=CC2N=C(N)SC=2C=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].BrC1C=CC2N=C(NC(=O)C)SC=2C=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C:23](=[O:25])[CH3:24])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 851492-Benzothiazolamine, 6-bromo-HCID 3240669N-(6-bromo-1,3-benzothiazol-2-yl)acetamideHCID 203571127-Bromo-1,3-benzothiazol-2-amine

Produkt 1

HCID 57584914N-(7-bromobenzo[d]thiazol-2-yl)acetamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The mixture (1.02 g, 4.45 mmol) of 7-bromobenzo[d]thiazol-2-amine and 6-bromobenzo[d]thiazol-2-amine and DMAP (620.6 mg, 5.079 mmol) were suspended in DCM (40 mL) and acetic anhydride (0.46 mL, 4.9 mmol) was added. The reaction was stirred under nitrogen at RT for 2 hours and was then quenched with 1 N HCl (25 mL). The layers were separated, and the aqueous phase was extracted with DCM, and the organic extracts were washed with 1 N HCl, dried over sodium sulfate, filtered, and concentrated to provide the mixture (865 mg, 72% yield) of N-(7-bromobenzo[d]thiazol-2-yl)acetamide and N-(6-bromobenzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 271 (MH+, 79Br), 273 (MH+, 81Br). Calculated exact mass for C9H7BrN2S: 270 (79Br), 272 (81Br).

Aufarbeitung

  1. customwas then quenched with 1 N HCl (25 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with DCM
  4. washthe organic extracts were washed with 1 N HCl
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-676de2c98c8446698854ab6e1ba52e74
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928140B2

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