Triphenylphosphine → HCID 21914748, compound

HRID 2117836Notes

Reaction equation

HRID 2117836 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]CCCC.[K+].[CH:37]([C:39]1[N:40]=[C:41]([NH:44][C:45](=[O:47])[CH3:46])[S:42][CH:43]=1)=O>O.C(OCC)(=O)C.CN(C)C=O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:37]/[C:39]2[N:40]=[C:41]([NH:44][C:45](=[O:47])[CH3:46])[S:42][CH:43]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromideHCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamideHCID 23699084Potassium butoxide

Product 1

HCID 21914748HCID 21914748, compoundYield 91.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitrobenzyl bromide (6.35 g), triphenylphosphine (7.71 g) and N,N-dimethylformamide (50 ml) was stirred for 5 hours at room temperature. To the mixture were added potassium butoxide (3.96 g), and then N-(4-formyl-1,3-thiazol-2-yl)acetamide (5.0 g) prepared in a similar manner according to Step 4 of Production Example 1, and the mixture was stirred for 13 hours at the same temperature. The reaction mixture was poured into ethyl acetate (200 ml) and water (200 ml). The organic layer was washed with water (20 ml), dried over sodium sulfate and concentrated in vacuo. The crystalline residue was collected and washed with 30% ethyl acetate/diisopropyl ether to give N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide (7.8 g).

Workup

  1. stirringthe mixture was stirred for 13 hours at the same temperature
  2. washThe organic layer was washed with water (20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crystalline residue was collected
  6. washwashed with 30% ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-64b5e79c2df6471fac2f6dea5a3215a4
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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