1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19347998, compound

HRID 1637191Notes

Reaction equation

HRID 1637191 reaction equation
N12CCCN=C1CCCCC2.Cl[C:13]1[C:14]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][C:15]=2[S:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([SH:37])[CH:34]=[CH:35][CH:36]=1>CN(C)C=O>[OH:28][CH2:27][C:24]1[CH:25]=[CH:26][C:14]2[C:13]([S:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([O:30][CH3:29])[CH:32]=3)=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:16][C:15]=2[CH:23]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 849893-MethoxybenzenethiolHCID 19347978HCID 19347978, compound

Product 1

HCID 19347998HCID 19347998, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU--1.1 ml, 7.23 mmol) was added to a mixture of ethyl 3-(chloro)-6-(hydroxymethyl)benzo[b]thiophene-2-carboxylate (Preparation 15--1.63 g, 6.02 mmol) and 3-methoxybenzenethiol (1.1 ml, 9.03 mmol) in anhydrous dimethylformamide (8 ml) under a nitrogen atmosphere. The solution was stirred at ambient temperature for 18 hours, and then heated to 60° C. for 3 hours. The solution was partitioned between diethyl ether and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was crystallised from diethyl ether and hexane to give the title compound as a colourless solid (1.77 g).

Workup

  1. temperatureheated to 60° C. for 3 hours
  2. customThe solution was partitioned between diethyl ether and water
  3. customThe organics were separated
  4. washwashed with water
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated under reduced pressure
  7. customThe residue was crystallised from diethyl ether and hexane

Sources & evidence

ORD record
ord-c921e6483042445d85479e07979ce04f
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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