Thioacetamide → HCID 86584929, compound

HRID 2308495Notes

Reaction equation

HRID 2308495 reaction equation
[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:14](=O)[CH2:15]Br)=[CH:12][CH:11]=[C:10]([O:18][CH3:19])[C:8]=2[N:9]=1.[C:21]([NH2:24])(=[S:23])[CH3:22]>O1CCOCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:14]3[N:24]=[C:21]([CH3:22])[S:23][CH:15]=3)=[CH:12][CH:11]=[C:10]([O:18][CH3:19])[C:8]=2[N:9]=1

Participants

5

Reactant 2

HCID 2723949ThioacetamideHCID 86584930HCID 86584930, compound

Product 1

HCID 86584929HCID 86584929, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1.3 g of (7-bromoacetyl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester (0.0036 Mol) and 0.27 g of thioacetamide (0.0036 Mol) were dissolved in dioxane (30 ml) and stirred for 4 hrs. at 70° C. After evaporation of half of the solvent water (40 ml) was added and the pH adjust to 7 with sat. NaHCO3. A solid precipitated, which was isolated and then subjected to column chromatography on silicagel using ethyl acetate as eluent. The title product was isolated as an off-white solid (27%); F.p.: 186-188° C.

Workup

  1. customat 70° C
  2. customAfter evaporation of half of the solvent water (40 ml)
  3. additionwas added
  4. customA solid precipitated
  5. customwhich was isolated

Sources & evidence

ORD record
ord-9ed2e8cc8b854b3b87e2176e6651e3ae
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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