HCID 22283192, compound → HCID 178488787, compound

HRID 1060300Notes

Reaction equation

HRID 1060300 reaction equation
Br[CH2:2][C: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)=O.[C:20]([O:24][C:25]([NH:27][C:28]([NH2:30])=[NH:29])=[O:26])([CH3:23])([CH3:22])[CH3:21]>C(#N)C>[C:20]([O:24][C:25]([NH:27][C:28]1[NH:29][CH:2]=[C:3]([C:5]2[C:13]3[S:12][C:11]([NH:14][C:15](=[O:17])[OH:16])=[N:10][C:9]=3[C:8]([O:18][CH3:19])=[CH:7][CH:6]=2)[N:30]=1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 22283192HCID 22283192, compoundHCID 178454308HCID 178454308, compound

Product 1

HCID 178488787HCID 178488787, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.25 g of (7-bromoacetyl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyll ester (0.0007 Mol) and 0.33 g of tert-butoxycarbonylguanidine (0.0021 Mol) were heated to reflux in acetonitril (3 ml) for 3 hrs. After evaporation of the solvent the residue was triturated with water (10 ml) and filtered. The filtrate was evaporated and the residue subjected to column chromatography (silicagel, ethyl-acetate/hexanes 1:1) to yield the title compound as a white solid (17%); F.p.: 255-265° C.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas triturated with water (10 ml)
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-327fc0b09c3e426fad0a12e4d1a4817e
Source dataset
uspto-grants-2003_02
Patent number
US06521754B2

Reaction notes

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