Hydrochloric Acid → HCID 12093204, compound

HRID 1270470Notes

Reaction equation

HRID 1270470 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH2:13][NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:8]([CH3:19])=[CH:7]2.[OH2:20].Cl.[C:22](Cl)(=[O:26])C(Cl)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH2:13][NH:14][S:15]([CH3:18])(=[O:16])=[O:17])[C:8]([CH3:19])=[C:7]2[C:22]([OH:26])=[O:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 65578Oxalyl chlorideHCID 12096337HCID 12096337, compound

Product 1

HCID 12093204HCID 12093204, compound

Conditions

Temperature
120 °C

Procedure

Under nitrogen, 2 g of 7-chloro-2-methyl-1-[3-(methylsulfonylamino)propyl]indole are dissolved in 16 ml of TCE at AT and 0.645 ml of oxalyl chloride in 7 ml of TCE is added. The mixture is heated at 120° C. for 16 hours and then cooled to AT. The reaction medium is diluted by adding 20 ml of water and is then poured onto 50 ml of a 10% HCl solution. The mixture is separated by settling out and the aqueous phase is then washed with DCM. The organic phases are combined and then washed with a saturated NaCl solution. Drying over Na2SO4 followed by concentration to dryness are performed and the product is purified by chromatography on silica, elution being carried out with CH2Cl2-MeOH (95/5; v/v). 1.33 g of the expected compound are obtained.

Workup

  1. additionis added
  2. temperaturecooled to AT
  3. additionThe reaction medium is diluted
  4. customThe mixture is separated
  5. washthe aqueous phase is then washed with DCM
  6. washwashed with a saturated NaCl solution
  7. dry with materialDrying over Na2SO4
  8. concentrationfollowed by concentration to dryness
  9. customthe product is purified by chromatography on silica, elution

Sources & evidence

ORD record
ord-302ccc1bc4134d7aa87d4cc8af3fa25c
Source dataset
uspto-grants-2007_04
Patent number
US07202268B2

Reaction notes

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