Hydrochloric Acid → E 7820

HRID 2355780Notes

Reaction equation

HRID 2355780 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]#[N:12].[C:14]([C:16]1[CH:17]=[C:18]([S:22](Cl)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1)#[N:15].N1C=CC=CC=1.Cl>C(OC)(=O)C.O.CC(O)CC>[C:11]([C:7]1[C:6]2[C:10](=[C:2]([NH:1][S:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([C:14]#[N:15])[CH:17]=3)(=[O:24])=[O:23])[CH:3]=[CH:4][C:5]=2[CH3:13])[NH:9][CH:8]=1)#[N:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 117152477-amino-4-methyl-1H-indole-3-carbonitrile

Product 1

HCID 196970E 7820

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6568(+-)-2-ButanolSolventHCID 6584Methyl AcetateSolvent

Conditions

Temperature
7 °C

Procedure

To a suspension of 5.0 g (29 mmol) of the 7-amino-3-cyano-4-methyl-1H-indole obtained in Example 2A and 6.48 g (32 mmol) of 3-cyanobenzenesulfonyl chloride [CAS No. 56542-67-7] in 150 mL of methyl acetate, were added 75 mL of water and 2.83 mL (35 mmol) of pyridine, followed by stirring for 2 hours and 40 minutes. After adding 0.73 mL (9 mmol) of concentrated hydrochloric acid to the reaction mixture, liquid-liquid separation was performed and the organic layer was washed with a mixture of 75 mL of water and 17.5 mL of ethanol. Activated carbon was added to the organic layer and the mixture was stirred at 45-50° C. for 30 minutes, and then filtered and concentrated. To thus obtained crude crystals were added 96 mL of 2-butanol and 24 mL of water for dissolution at 75° C., and the solution was cooled to 7° C. at approximately 10° C./hr and stirred overnight. The precipitated crystals were collected by filtration and washed twice with 10 mL of 2-butanol to give 8.17 g (wet weight) of crystals of the title compound. The crystals were dried under reduced pressure at 70° C. for 2 hours to give 7.54 g of crystals of the title compound.

Workup

  1. customto the reaction mixture, liquid-liquid separation
  2. washthe organic layer was washed with a mixture of 75 mL of water and 17.5 mL of ethanol
  3. additionActivated carbon was added to the organic layer
  4. stirringthe mixture was stirred at 45-50° C. for 30 minutes
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customTo thus obtained crude crystals
  8. dissolutionfor dissolution at 75° C.
  9. stirringstirred overnight
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed twice with 10 mL of 2-butanol

Sources & evidence

ORD record
ord-2ce3006d23db4f0c83ae071d9ca64698
Source dataset
uspto-grants-2010_07
Patent number
US07754894B2

Reaction notes

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