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

HRID 2077518Notes

Reaction equation

HRID 2077518 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.[C:12](OC(=O)C)(=[O:14])[CH3:13]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 203571127-Bromo-1,3-benzothiazol-2-amine

Product 1

HCID 57584914N-(7-bromobenzo[d]thiazol-2-yl)acetamideYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

7-Bromobenzo[d]thiazol-2-amine (550 mg, 2.40 mmol) and DMAP (330 mg, 2.70 mmol) were suspended in DCM (12 mL) and acetic anhydride (0.25 mL, 2.7 mmol) was added. The reaction was stirred under nitrogen at RT for 6 hours, the suspension was filtered, and the solid was washed with DCM. The solid was collected, and the filtrate was concentrated and treated with MeOH. This batch of solid was also collected by filtration. The filtrate was concentrated, and filtered through silica gel (40:1 DCM/MeOH) to provide additional products. The collected solids were combined to afford N-(7-bromobenzo[d]thiazol-2-yl)acetamide (433 mg, 67% yield) as a white solid. MS (ESI pos. ion) m/z: 271 (MH+, 79Br), 273 (MH+, 81Br). Calculated exact mass for C9H7BrN2S: 270 (79Br), 272 (81Br).

Workup

  1. filtrationthe suspension was filtered
  2. washthe solid was washed with DCM
  3. customThe solid was collected
  4. concentrationthe filtrate was concentrated
  5. additiontreated with MeOH
  6. filtrationThis batch of solid was also collected by filtration
  7. concentrationThe filtrate was concentrated
  8. filtrationfiltered through silica gel (40:1 DCM/MeOH)
  9. customto provide additional products

Sources & evidence

ORD record
ord-b3f086cbe6544718b50d8cf88da33c87
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…