Trifluoroacetic acid → HCID 67443457, compound

HRID 1666900Notes

Reaction equation

HRID 1666900 reaction equation
CN(C)[CH:3]=[CH:4][N+:5]([O-:7])=[O:6].C(O)(C(F)(F)F)=O.[C:16]1([S:22]([C:25]2[CH:33]=[C:32]3[C:28]([CH:29]=[CH:30][NH:31]3)=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[N+:5]([CH:4]=[CH:3][C:29]1[C:28]2[C:32](=[CH:33][C:25]([S:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:23])=[O:24])=[CH:26][CH:27]=2)[NH:31][CH:30]=1)([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 518458Ethenamine, N,N-dimethyl-2-nitro-HCID 674423236-benzenesulfonyl-1H-indole

Product 1

HCID 67443457HCID 67443457, compound

Procedure

Combine 1-dimethylamino-2-nitroethylene (676.9 mg, 5.83 mmol) and TFA (9.0 ml) and stir until dissolved. Add 6-benzenesulfonyl-1H-indole (1.5 g, 5.83 mmol) and stir at ambient temperature. After 24 hours, pour the reaction mixture into ice/water and adjust to pH 8. After stirring, filter the precipitate, wash with water, and dry to give the title compound as a yellow powder: mp 110° C., dec. MS (ACPI): m/e 329.0 (M+1). Analysis for C16H12N2O4S: Calcd: C, 58.53; H, 3.68; N, 8.53. found: C, 58.54; H, 3.83; N, 7.85.

Workup

  1. dissolutionuntil dissolved
  2. filtrationfilter the precipitate
  3. washwash with water
  4. customdry

Sources & evidence

ORD record
ord-93413329479d4ab9acd1053d6013b39f
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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