Trifluoroacetic acid → 3-(2-Nitrovinyl)-6-methanesulfonyl-1H-indole

HRID 1666899Notes

Reaction equation

HRID 1666899 reaction equation
CN(C)[CH:3]=[CH:4][N+:5]([O-:7])=[O:6].C(O)(C(F)(F)F)=O.[CH3:16][S:17]([C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[CH:25][NH:26]2)=[CH:22][CH:21]=1)(=[O:19])=[O:18]>>[N+:5]([CH:4]=[CH:3][C:24]1[C:23]2[C:27](=[CH:28][C:20]([S:17]([CH3:16])(=[O:19])=[O:18])=[CH:21][CH:22]=2)[NH:26][CH:25]=1)([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 518458Ethenamine, N,N-dimethyl-2-nitro-HCID 27610676-methanesulfonyl-1H-indole

Product 1

HCID 674417603-(2-Nitrovinyl)-6-methanesulfonyl-1H-indole

Procedure

Combine 1-dimethylamino-2-nitroethylene (892.1 mg, 7.68 mmol) and TFA (9.0 ml) and stir until dissolved. Add 6-methanesulfonyl-1H-indole (1.5 g, 7.68 mmol) and stir at ambient temperature. After 24 hours, pour the reaction mixture into ice/water, extract with ethyl acetate, then wash ethyl acetate with brine and saturated sodium bicarbonate. Filter, wash, and dry the precipitate to give the title compound as a yellow powder: mp>250° C. MS (ACPI): m/e 267.0 (M+1). Analysis for C11H10N2O4S: Calcd: C, 49.62; H, 3.79; N, 10.52. found: C, 49.86; H, 3.97; N, 10.25.

Workup

  1. dissolutionuntil dissolved
  2. extractionextract with ethyl acetate
  3. filtrationFilter
  4. washwash
  5. customdry the precipitate

Sources & evidence

ORD record
ord-5177c7d05ad340fa96923e29eaea6d0a
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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