1-(6-Phenylacetylenyl-2-benzothiazolyl)-3-ethylurea → 1-(6-(2(Z)-Phenylvinyl)-2-benzothiazolyl)-3-ethylurea

HRID 9133

Reaction equation

HRID 9133 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:23]=[CH:22][C:12]3[N:13]=[C:14]([NH:16][C:17]([NH:19][CH2:20][CH3:21])=[O:18])[S:15][C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(O)C>[C:1]1(/[CH:7]=[CH:8]\[C:9]2[CH:23]=[CH:22][C:12]3[N:13]=[C:14]([NH:16][C:17]([NH:19][CH2:20][CH3:21])=[O:18])[S:15][C:11]=3[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 219855451-(6-Phenylacetylenyl-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 865889731-(6-(2(Z)-Phenylvinyl)-2-benzothiazolyl)-3-ethylureaYield 41%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-(6-phenylacetylenyl-2-benzothiazolyl)-3-ethylurea (0.032 g, 83% purity by weight, 0.083 mmol) and Lindlar catalyst (0.030 g, 5% weight purity, 0.012 mmol, 0.15 eq) in 2 mL ethanol was purged with nitrogen gas, followed by bubbling of hydrogen gas. It was stirred under hydrogen atmosphere for about 36 hours. The mixture was taken up in 10 mL MeOH, filtered, concentrated, and purified by preparative TLC to give 0.011 g (41%) of the desired compound. LC/MS 324 (M+1); LC retention time 2.84 min.

Workup

  1. customwas purged with nitrogen gas
  2. customby bubbling of hydrogen gas
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by preparative TLC

Sources & evidence

ORD record
ord-b034843c1eae49b58ee346d1b1960c87
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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