Triphenylphosphine → HCID 178479726, compound

HRID 1595412Notes

Reaction equation

HRID 1595412 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:24]([NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)=[O:25])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:51]N1C(=O)CCC1=O>O1CCCC1>[ClH:51].[Cl:51][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:24]([NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)=[O:25])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11776Triphenylphosphine2×HCID 31398Chlorosuccinimide2×HCID 178522566HCID 178522566, compound

Product 1

HCID 178479726HCID 178479726, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Hydroxymethylphenyl)-2-(1-naphthyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (1.0 g) obtained in Example 61 was dissolved in tetrahydrofuran (200 ml), and triphenylphosphine (1.24 g) and N-chlorosuccinimide (633 mg) were added. The mixture was stirred for 15 min and triphenylphosphine (1.24 g) and N-chlorosuccinimide (633 mg) 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 suspended in acetone (30 ml) and 1 M hydrochloric acid—ether solution (3 ml) was added. The solvent was evaporated and ethyl acetate was added to the obtained residue. The resulting crystals were collected by filtration to give 5-(4-chloromethylphenyl)-2-(1-naphthyl)-N-(2-thiazolyl)imidazole-4-carboxamide hydrochloride (580 mg), 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. addition1 M hydrochloric acid—ether solution (3 ml) was added
  7. customThe solvent was evaporated
  8. additionethyl acetate was added to the obtained residue
  9. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-86b242718ce94a3ea3aae265d9da8c5f
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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