Triphenylphosphine → HCID 178424023, compound

HRID 1595389Notes

Reaction equation

HRID 1595389 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:11]([C:13]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]O)=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[ClH:28].[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:9][C:10]([C:21]4[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=4)=[C:11]([C:13]([NH:15][C:16]4[S:17][CH:18]=[CH:19][N:20]=4)=[O:14])[N:12]=3)=[CH:4][CH:3]=2)=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 133974-Chlorobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178424021HCID 178424021, compound

Product 1

HCID 178424023HCID 178424023, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Hydroxyphenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.38 g) obtained in Example 23, 4-chlorobenzyl alcohol (0.14 g) and triphenylphosphine (0.26 g) were dissolved in tetrahydrofuran (25 ml) and diethyl azodicarboxylate (0.16 ml) was added. The mixture was stirred for 40 hr. Water was added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried. The solvent was evaporated and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3). The obtained residue was converted to hydrochloride to give 2-(4-(4-chlorophenylmethyloxy)-phenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide hydrochloride (61 mg), melting point 203-205° C. (decomposition).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. customdried
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-3b0b6769846f433fba49f76d8102177d
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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