Phenol → HCID 10113034, compound

HRID 1058941Notes

Reaction equation

HRID 1058941 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:11]([CH:19]([CH3:21])[CH3:20])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=2[CH2:15]O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:11]([CH:19]([CH3:21])[CH3:20])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=2[CH2:15][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[OH:28])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 514434HCID 514434, compoundHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 10113034HCID 10113034, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 100 mg of 4-(3,5-dichlorophenylthio)-5-(hydroxymethyl)-3-isopropyl-1-methyl-1,3-dihydro-2-imidazolone, 30 mg of phenol and 100 mg of triphenylphosphine in 5 mL of tetrahydrofuran at 0° C. was added 70 μL of diisopropylazodicarboxylate in 5 mL of tetrahydrofuran over 20 min. The reaction was stirred overnight warming to room temperature. The mixture was then diluted with ethyl acetate and washed with 0.5N hydrochloric acid solution then 0.5N sodium hydroxide solution, dried, concentrated and purified by flash chromatography eluting with 3:1 hexane: ethyl acetate to give 16 mg of a colourless oil. Mass spectrum (ES) m/z 423 [M+H]+.

Workup

  1. washwashed with 0.5N hydrochloric acid solution
  2. dry with material0.5N sodium hydroxide solution, dried
  3. concentrationconcentrated
  4. custompurified by flash chromatography
  5. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-991b06e9cbf04e38b1cc7fe222af7da0
Source dataset
uspto-grants-2003_02
Patent number
US06518293B2

Reaction notes

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