Methanimidic acid, N-phenyl-, ethyl ester → HCID 9820710, compound

HRID 1729046Notes

Reaction equation

HRID 1729046 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][S:14]([NH:17][CH3:18])(=[O:16])=[O:15])[CH:11]=2)[NH:6][CH:5]=1.[C:19]1([N:25]=[CH:26]OCC)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[C:19]1([NH:25][CH:26]=[N:1][CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][S:14]([NH:17][CH3:18])(=[O:15])=[O:16])[CH:11]=3)[NH:6][CH:5]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 111236Methanimidic acid, N-phenyl-, ethyl esterHCID 9813988Didesmethyl sumatriptan

Product 1

HCID 9820710HCID 9820710, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.67 g (0.01 m) of 3-(2-aminoethyl)-1H-indole-5-yl-N-methyl methane sulphonamide and 10 mL of acetone were charged in a 25 mL round bottom flask. 1.64g (0.01 m) of ethyl N-phenylformimidate were added and the mixture was stirred at room temperature for 24 hours. When the reaction was deemed to have terminated, as per the TLC control (eluant: butanol/acetic acid/H2O 65/13/22) the acetone was concentrated to dryness and the oil obtained was crystallized from toluene. It was filtered, was washed with 10 mL of toluene and dried in a current of air at 50° C. to give 2.5 g of 3-[2-(N-phenylaminomethyleneamino)ethyl]-1H-indole-5-yl-N-methyl methane sulphonamide, in the form of a cream colored solid, representing a 67% yield. M.p.=72°-73° C.

Workup

  1. customto have terminated, as per the TLC control (eluant: butanol/acetic acid/H2O 65/13/22) the acetone
  2. concentrationwas concentrated to dryness
  3. customthe oil obtained
  4. customwas crystallized from toluene
  5. filtrationIt was filtered
  6. washwas washed with 10 mL of toluene
  7. customdried in a current of air at 50° C.

Sources & evidence

ORD record
ord-c682c3eb39564834a4ed678350945984
Source dataset
uspto-grants-1994_07
Patent number
US05331005

Reaction notes

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