Triethylamine → HCID 53672970, compound

HRID 476829Notes

Reaction equation

HRID 476829 reaction equation
CS(Cl)(=O)=O.O[CH2:7][CH2:8][C:9]1[CH:13]=[C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[NH:11][C:10]=1[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C.[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.[K]>C(Cl)Cl.CN(C=O)C>[C:31]1(=[O:41])[N:35]([CH2:7][CH2:8][C:9]2[CH:13]=[C:12]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)[NH:11][C:10]=2[C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 24194345Phthalimide potassium saltHCID 54330269HCID 54330269, compound

Product 1

HCID 53672970HCID 53672970, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution containing 0.75 g of methanesulfonyl chloride in 25 mL of CH2Cl2 was added to a stirred solution containing 0.8 g (3.3 mmol) of 3-(2-hydroxyethyl)-2,5-dithienylpyrrole (XX) and 3 mL of triethylamine in 25 mL of methylene chloride (CH2Cl2) maintained at 0° C. under an inert argon gas atmosphere. The mixture was stirred for 2 hours at 0° C., followed by treatment with a solution containing 8 g (40 mmol) of potassium phthalimide in 50 mL of DMF. The resulting mixture was heated at 40° C. overnight. After cooling to room temperature, the mixture was filtered, and the solvents of the filtrate evaporated in vacuo in the presence of with 20 g of SiO2 -60. The solid absorbed on the SiO2 was chromatographed on a 100 g column of SiO2 -60 that was equilibrated and eluted with a 1% dioxane-toluene solvent mixture. Fractions having volumes of 20 mL were collected, and fractions numbered 10 through 25, containing the product (XXI), were combined, then concentrated to yield 860 mg of an oil (64% yield). An analytical sample of compound XXI (mp 174°-175° C.) was recrystallized from diethyl ether.

Workup

  1. additionwas added to a stirred solution
  2. temperatureThe resulting mixture was heated at 40° C. overnight
  3. temperatureAfter cooling to room temperature
  4. filtrationthe mixture was filtered
  5. customthe solvents of the filtrate evaporated in vacuo in the presence of with 20 g of SiO2 -60
  6. customThe solid absorbed on the SiO2
  7. customwas chromatographed on a 100 g column of SiO2 -60
  8. washeluted with a 1% dioxane-toluene solvent mixture
  9. customwere collected
  10. additioncontaining the product (XXI)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f05254cd254c48f19f5d1b740fd041ae
Source dataset
uspto-grants-1989_12
Patent number
US04886625

Reaction notes

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