Water → 6-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)benzo[d]thiazole

HRID 1930270Notes

Reaction equation

HRID 1930270 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[CH3:12][C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH3:17].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.O>C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([N:9]3[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]3[CH3:12])[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80352,5-HexanedioneHCID 851492-Benzothiazolamine, 6-bromo-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 574939166-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)benzo[d]thiazoleYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution 6-bromobenzo[d]thiazol-2-amine (5.75 g, 25.1 mmol), hexane-2,5-dione (2.95 mL, 25.1 mmol), and PPTS (0.95 g, 3.76 mmol) in benzene (100 ml) was refluxed for 16 h while water was removed with a Dean-Stark trap. The cooled mixture was poured into EtOAc (100 mL) and extracted with saturated aq. NaHCO3 (2×100 mL) and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 9:1 EtOAc:hexanes as the eluent to give the title compound as an orange oil (6.46 g, 84%).

Workup

  1. customwas removed with a Dean-Stark trap
  2. additionThe cooled mixture was poured into EtOAc (100 mL)
  3. extractionextracted with saturated aq. NaHCO3 (2×100 mL) and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel using 9:1 EtOAc

Sources & evidence

ORD record
ord-f6333cffe20149c8861605eb7cf2ee68
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Reaction notes

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