HCID 22283318, compound → HCID 22283192, compound

HRID 1060297Notes

Reaction equation

HRID 1060297 reaction equation
[Br:1][CH2:2][CH:3]([C:5]1[C:13]2[S:12][C:11]([NH:14][C:15](=[O:17])[OH:16])=[N:10][C:9]=2[C:8]([O:18][CH3:19])=[CH:7][CH:6]=1)[OH:4]>C(Cl)(Cl)Cl.O=[Mn]=O>[Br:1][CH2:2][C:3]([C:5]1[C:13]2[S:12][C:11]([NH:14][C:15](=[O:16])[OH:17])=[N:10][C:9]=2[C:8]([O:18][CH3:19])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 22283318HCID 22283318, compound

Product 1

HCID 22283192HCID 22283192, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

1.6 g of rac-[7-(2-bromo-1 -hydroxy-ethyl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyll ester (0.0044 Mol) were dissolved in CHCl3 (100 ml) and treated with 3.8 g of MnO2 (0.044 Mol) for 3 hrs. at 70° C. The hot reaction mixture was filtered and subsequently concentrated. The crude product was crystallized from Et2O to yield the title compound as a beige solid (73%); F.p.: 250-260° C. (dec.).

Workup

  1. customat 70° C
  2. filtrationThe hot reaction mixture was filtered
  3. concentrationsubsequently concentrated
  4. customThe crude product was crystallized from Et2O

Sources & evidence

ORD record
ord-58989a228bd241b1b5af991a333b4292
Source dataset
uspto-grants-2003_02
Patent number
US06521754B2

Reaction notes

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