Phenacyl bromide → HCID 19347459, compound

HRID 1638169Notes

Reaction equation

HRID 1638169 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O>CN(C)C=O>[C:16]1([C:14]2[N:1]=[C:2]3[N:6]([CH:13]=2)[C:5]2[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[S:3]3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 5878502-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one2×

Product 1

HCID 19347459HCID 19347459, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-4,5-dihydrobenzothiazole-7(6H)-one (18 g) prepared in the above (A) was dissolved into dimethylformamide (250 ml), and 2-bromoacetophenone (21,83 g) was added thereto followed by heating to reflux for 12-15 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and placed into distilled water. The resulting precipitates were filtered, neutralized with sodium hydroxide solution, filtered, washed with ethyl acetate (100 ml), and dried to give the titled compound (21.25 g, 76%).

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureto reflux for 12-15 hours
  4. customAfter completion of the reaction
  5. distillationinto distilled water
  6. customThe resulting precipitates
  7. filtrationwere filtered
  8. filtrationfiltered
  9. washwashed with ethyl acetate (100 ml)
  10. customdried

Sources & evidence

ORD record
ord-fdfe4a661ca94277be2f06364f5123ed
Source dataset
uspto-grants-2000_03
Patent number
US06043373

Reaction notes

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