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

HRID 2077515

Reaction equation

HRID 2077515 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-676de2c98c8446698854ab6e1ba52e74
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Linked notes

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