Triphenylphosphine → HCID 178522570, compound

HRID 1595413Notes

Reaction equation

HRID 1595413 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:23]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:24])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:50]N1C(=O)CCC1=O>O1CCCC1>[Cl:50][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:23]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:24])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11776Triphenylphosphine2×HCID 31398Chlorosuccinimide2×HCID 178522573HCID 178522573, compound

Product 1

HCID 178522570HCID 178522570, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Hydroxymethylphenyl)-2-(4-nitrophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (2.67 g) obtained in Example 93 was dissolved in tetrahydrofuran (300 ml) and triphenylphosphine (3.33 g) and N-chlorosuccinimide (1.70 g) were added. The mixture was stirred for 15 min and triphenylphosphine (3.33 g) and N-chlorosuccinimide (1.70 g) were added. The mixture was stirred for 30 min. The reaction mixture was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and, after drying, concentrated. The obtained residue was recrystallized from ethyl acetate to give 5-(4-chloromethylphenyl)-2-(4-nitrophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (2.60 g), melting point 280° C. or above.

Workup

  1. stirringThe mixture was stirred for 30 min
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. customafter drying
  5. concentrationconcentrated
  6. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f2142612530445388882b4627f60ae6f
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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