Carbon Dioxide → HCID 14836266, compound

HRID 1088626Notes

Reaction equation

HRID 1088626 reaction equation
C([Li])CCC.O1CCCC1.[Cl:11][C:12]1[CH:29]=[CH:28][C:15]2[S:16][CH:17]=[C:18]([CH2:19][N:20]([CH2:22][CH:23]([O:26][CH3:27])[O:24][CH3:25])[CH3:21])[C:14]=2[CH:13]=1.[C:30](=[O:32])=[O:31]>CO>[Cl:11][C:12]1[CH:29]=[CH:28][C:15]2[S:16][C:17]([C:30]([OH:32])=[O:31])=[C:18]([CH2:19][N:20]([CH2:22][CH:23]([O:24][CH3:25])[O:26][CH3:27])[CH3:21])[C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8028Tetrahydrofuran2×HCID 14836265HCID 14836265, compoundHCID 178418339Butyllithium

Product 1

HCID 14836266HCID 14836266, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-30 °C

Procedure

Butyllithium in tetrahydrofuran (2.6M, 0.04 mol) was added slowly to a solution of 5-chloro-3-[N-(2,2-dimethoxyethyl)-N-methyl(aminomethyl)]benzo[b]thiophene (10 g, 0.033 mol) in freshly distilled tetrahydrofuran (100 ml) stirred at -30° C. under argon. The mixture was stirred for 30 minutes, treated with dry carbon dioxide for 5 minutes and allowed to warm to 25° C. The mixture was treated with methanol, poured into ice water and extracted with ethyl ether. The aqueous phase was adjusted to pH 7.5 and extracted with methylene chloride. The organic phase was washed with water, dried with magnesium sulfate and concentrated to give 6.0 g (54%) of 5-chloro-3-[N-(2,2-dimethoxyethyl)-N-methyl(aminomethyl)]benzo[b]thiophene-2-carboxylic acid.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. temperatureto warm to 25° C
  3. extractionextracted with ethyl ether
  4. extractionextracted with methylene chloride
  5. washThe organic phase was washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-33c54f84aad046d6a99f54376a2b0626
Source dataset
uspto-grants-1990_10
Patent number
US04963547

Reaction notes

Loading…