Phenacyl bromide → HCID 18536787, compound

HRID 2298604Notes

Reaction equation

HRID 2298604 reaction equation
[NH2:1][C:2](=[S:12])[C:3]1[CH:4]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[S:6][CH:7]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O>CC(C)=O>[C:17]1([C:15]2[N:1]=[C:2]([C:3]3[CH:4]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[S:6][CH:7]=3)[S:12][CH:14]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 18537039HCID 18537039, compound

Product 1

HCID 18536787HCID 18536787, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 150 mg (0.745 mmol) of methyl 4-(aminothioxomethyl)-thiophene-2-carboxylate (as prepared in the previous step) in 6 mL of acetone was added 148 mg (0.745 mmol) of 2-bromoacetophenone. After refluxing for 2 h, the mixture was concentrated by boiling to a volume of ca. 2 mL. The resulting mixture was cooled (−10° C.) and filtered washing with cold acetone (2×0.5 mL). A second crop was obtained from the mother liquors and the combined crops dried to afford the title compound as a beige solid (202 mg, 90%). 1H-NMR (300 MHz, DMSO-d6) δ8.56 (d, 1H, J=1.5 Hz), 8.25 (d, 1H, J=1.5 Hz), 8.18 (s, 1H), 8.04 (d, 2H, J=7 Hz), 7.48 (t, 2H, J=7 Hz), 7.38 (t, 1H, J=7 Hz), and 3.89 (s, 3H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C15H11NO2S2: 302.0 (M+H). Found: 301.8.

Workup

  1. temperatureAfter refluxing for 2 h
  2. concentrationthe mixture was concentrated
  3. filtrationfiltered
  4. washwashing with cold acetone (2×0.5 mL)
  5. customA second crop was obtained from the mother liquors
  6. customthe combined crops dried

Sources & evidence

ORD record
ord-d083ad0f226546ba9c562ddca43ebe41
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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