Hydrochloric Acid → HCID 20270200, compound

HRID 485355Notes

Reaction equation

HRID 485355 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)(O)=O.S(N)([NH2:26])(=O)=O.S(Cl)(Cl)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>S1(CCCC1)(=O)=O>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)#[N:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 82267SulfamideHCID 521998p-Toluenesulfonic acid monohydrateHCID 134903525-[1-(Pyridin-3-yl)-1H-indol-3-yl]pentanoic acid

Product 1

HCID 20270200HCID 20270200, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A suspension of 26.6 g of 3-(4-carboxybutyl)-N-(3-pyridyl)indole and 10.5 g of sulfamide in 90 ml of sulfolane is treated with 11.42 g of thionyl chloride at room temperature under nitrogen. The mixture is heated at 120° until gas evolution ceases and solid p-toluenesulfonic acid monohydrate (1.71 g) is added carefully. After heating an additional 3 hours at 120°, the reaction mixture is cooled, poured onto 200 g of ice and acidified with 130 ml of 1N hydrochloric acid. The aqueous phase is sequentially extracted with ethyl acetate (3×100 ml), made basic with solid sodium bicarbonate and reextracted with ethyl acetate (3×125 ml). The organic extracts are washed with 0.5N sodium hydroxide (5×50 ml), dried over sodium sulfate and evaporated to yield and oil which is chromatographed on 60 g of silica gel to yield 3-(4-cyanobutyl)-N-(3-pyridyl)indole.

Workup

  1. additionis added carefully
  2. temperatureAfter heating an additional 3 hours at 120°
  3. temperaturethe reaction mixture is cooled
  4. extractionThe aqueous phase is sequentially extracted with ethyl acetate (3×100 ml)
  5. washThe organic extracts are washed with 0.5N sodium hydroxide (5×50 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto yield
  9. customoil which is chromatographed on 60 g of silica gel

Sources & evidence

ORD record
ord-3b2423ece9a448408c6d0d562a94ebe3
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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