Water → HCID 22559553, compound

HRID 983352Notes

Reaction equation

HRID 983352 reaction equation
[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=2)=[O:11])=[N:6][CH:5]=1)([CH3:3])[CH3:2].CN(C)C(=N)N(C)C.[I-].[OH2:29]>CN(C)C=O>[OH:29][CH:4]([CH3:5])[C:1]#[C:2][C:15]1[CH:14]=[C:13]([NH:12][C:10]([NH:9][C:7]2[S:8][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][N:6]=2)=[O:11])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 30165Iodide IonHCID 664601,1,3,3-TetramethylguanidineHCID 22559497HCID 22559497, compound

Product 1

HCID 22559553HCID 22559553, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.2 g (0.56 mmol) of N-(5-isopropyl-1,3-thiazol-2-yl)-N′-(3-iodophenyl)urea in 3 ml of anhydrous N,N-dimethylformamide 0.6 ml of tetramethylguanidine, 0.088 ml (1.126 mmol) of D,L-1-butyn-3-ol, 19 mg (0.027 mmol) of bis(triphenylphosphine)palladium(II)dihydrochloride and 5.8 mg (0.03 mmol) of rameous iodide under argon were added successively. After 5 hours water was added and the mixture extracted with ethylacetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated, giving 0.116 g of the title compound as a yellowish solid.

Workup

  1. extractionthe mixture extracted with ethylacetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-032394f104d24afa8009dee5eb341a12
Source dataset
uspto-grants-2005_03
Patent number
US06863647B2

Reaction notes

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