Hydrochloric Acid → (5-Dimethylthiocarbamoyloxy-indol-1-yl)-acetic acid methyl ester

HRID 1296061Notes

Reaction equation

HRID 1296061 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[H-].[Na+].C(Cl)(=[S:20])N.Cl.[CH3:23][N:24]([CH:26]=O)[CH3:25]>>[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:26](=[S:20])[N:24]([CH3:25])[CH3:23])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 13773237Thiocarbamoyl chlorideHCID 20770839methyl (5-hydroxy-1H-indol-1-yl)acetate

Product 1

HCID 20770838(5-Dimethylthiocarbamoyloxy-indol-1-yl)-acetic acid methyl ester

Procedure

Compound 72B (9.12 g, 44.4 mmol) was dissolved in 50 ml DMF. NaH was added portionwise over 5 minutes. After stirring for 15 minutes a solution of thiocarbamoyl chloride (5.8 g, 46.7 mmol) in 25 ml DMF was added and allowed to stir for 2 h. 50 ml 2N HCl was added and the reaction was extracted 2×100 ml ether, washed 2×100 ml water, 1×100 ml brine, and filtered through silica. The product was eluted with 200 ml diethyl ether and concentrated. The precipitate was filtered and dried under vacuum for 16 h. MS m/z 293 (M+1).

Workup

  1. additionwas added
  2. extractionthe reaction was extracted 2×100 ml ether
  3. washwashed 2×100 ml water, 1×100 ml brine
  4. filtrationfiltered through silica
  5. washThe product was eluted with 200 ml diethyl ether
  6. concentrationconcentrated
  7. filtrationThe precipitate was filtered
  8. customdried under vacuum for 16 h

Sources & evidence

ORD record
ord-6a1f19aab1364b5e916662743fc5d571
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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