Hydrochloric Acid → HCID 23227018, compound

HRID 1956178Notes

Reaction equation

HRID 1956178 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]([CH3:20])([CH3:19])[CH:8]2[C:11]2[C:12]([S:17][CH3:18])=[N:13][CH:14]=[N:15][CH:16]=2)=[CH:4][CH:3]=1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>N1C=CC=CC=1>[CH3:19][C:7]1([CH3:20])[CH2:6][C:5]2[C:9](=[CH:10][C:2]([NH:1][S:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:29])=[O:28])=[CH:3][CH:4]=2)[CH:8]1[C:11]1[C:12]([S:17][CH3:18])=[N:13][CH:14]=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 18662979HCID 18662979, compound

Product 1

HCID 23227018HCID 23227018, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.0 g (3.5 mmol) of 5-(6-amino-2,2-dimethylindan-1-yl)-4-methylthiopyrimidine in 20 mL of dry pyridine was added with stirring 0.45 g (3.7 mmol) of benzenesulfonyl chloride. The mixture was allowed to react for 16 hr and was then poured into dilute aqueous hydrochloric acid with stirring. The resulting mixture was extracted with ether and the ethereal extract was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The remaining oil was diluted with a small amount of dichloromethane and then hexane was added. The precipitate that formed was collected by filtration and dried under reduced pressure to obtain 700 mg (88 percent of theory) of the title compound as a tan solid melting at 174°-176° C.

Workup

  1. customto react for 16 hr
  2. extractionThe resulting mixture was extracted with ether
  3. extractionthe ethereal extract
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. additionThe remaining oil was diluted with a small amount of dichloromethane
  8. additionhexane was added
  9. customThe precipitate that formed
  10. filtrationwas collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-48d118be15b8484da189da06d4c7e720
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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