1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54363513, compound

HRID 1637198Notes

Reaction equation

HRID 1637198 reaction equation
N12CCCN=C1CCCCC2.Cl[C:13]1[C:14]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)=[CH:23][C:15]=2[S:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH3:33][O:34][C:35]1[CH:36]=[C:37]([SH:41])[CH:38]=[CH:39][CH:40]=1>CN(C)C=O>[N:28]1([CH2:27][C:24]2[CH:25]=[CH:26][C:14]3[C:13]([S:41][C:37]4[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH3:33])[CH:36]=4)=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:16][C:15]=3[CH:23]=2)[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 849893-MethoxybenzenethiolHCID 54002689HCID 54002689, compound

Product 1

HCID 54363513HCID 54363513, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU--0.26 ml, 1.7 mmol) was added to a mixture of ethyl 3-chloro-6-(1H-1-imidazolylmethyl)benzo[b]thiophene-2-carboxylate (Preparation 11, 500 mg, 1.6 mmol) and 3-methoxybenzenethiol (0.29 ml, 2.3 mmol) in dimethylformamide (2 ml) under a nitrogen atmosphere. The solution was heated to 60° C. for 5 hours and then partitioned between ethyl acetate and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using 5% methanol in dichloromethane as eluant to give the title compound as a gum (615 mg).

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organics were separated
  3. washwashed with water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel using 5% methanol in dichloromethane as eluant

Sources & evidence

ORD record
ord-b5c64c74a84f4d18b3dda5a6399ce464
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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