Water → HCID 19699376, compound

HRID 863095Notes

Reaction equation

HRID 863095 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[O:26]C)[CH2:6][N:7]1[CH:11]=[CH:10][N:9]([CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)[C:8]1=[S:22].B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[OH:26])[CH2:6][N:7]1[CH:11]=[CH:10][N:9]([CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)[C:8]1=[S:22]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 19699568HCID 19699568, compound

Product 1

HCID 19699376HCID 19699376, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(3,4-dimethoxybenzyl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (900 mg, 2.37 mol), prepared as in Example 15, in methylene chloride was cooled to 0° C. under nitrogen and then boron tribromide (1M, 7.1 mL, 7.1 mmol) in an additional 10 mL of methylene chloride was added dropwise. The mixture was allowed to cool to room temperature, stirred for 16 hours and then slowly added to water. The organic layer was separated, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with methylene chloride/methanol (96:4) and then crystallized from methanol/ethanol/hexane to give 3-(3,4-dihydroxybenzyl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (520 mg), m.p. 173°-174° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel eluting with methylene chloride/methanol (96:4)
  6. customcrystallized from methanol/ethanol/hexane

Sources & evidence

ORD record
ord-f860e3ce191d4f51bcbe37feaaec3f00
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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