Water → 2-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole

HRID 8403Notes

Reaction equation

HRID 8403 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][CH:12]=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:27]=[C:28]([S:33]Cl)[CH:29]=[C:30]([Cl:32])[CH:31]=1.O>C(#N)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:33][C:28]2[CH:29]=[C:30]([Cl:32])[CH:31]=[C:26]([Cl:25])[CH:27]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 101305733,5-Dichlorobenzenesulfenyl chlorideHCID 178419054HCID 178419054, compound

Product 1

HCID 1784190342-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazoleYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

2-Benzyloxymethyl-4-isopropyl-1H-imidazole (7) (550 mg, 2.4 mmol), described as Reference Example 1 of WO 96/10019 was dissolved in a mixture of triethylamine 360 mg (3.6 mmol) and acetonitrile 4 ml. To the solution was added 3,5-dichlorobenzenesulfenyl chloride (3) 930 mg (4.4 mmol) at room temperature. The mixture was stirred for 30 minutes at room temperature and water (15 ml) and toluene (15 ml) were added thereto. The toluene layer was separated, washed with water 10 ml twice, and concentrated under reduced pressure. The obtained yellow oil was crystallized with diisopropyl ether 10 ml, filtered, and dried to yield the objective (8) 800 mg as a pale yellow crystal. Yield 82%.

Workup

  1. customThe toluene layer was separated
  2. washwashed with water 10 ml twice
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained yellow oil was crystallized with diisopropyl ether 10 ml
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-d703faf9a4724073854aea47b7f469a8
Source dataset
uspto-grants-2006_08
Patent number
US07087764B2

Reaction notes

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