Trifluoroacetic acid → HCID 86602625, compound

HRID 1371971Notes

Reaction equation

HRID 1371971 reaction equation
[CH3:1][N:2]([CH3:8])[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]=C3[C:28]([CH:29]=CN3)=[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][N:2]1[C:8]2[C:28](=[CH:27][CH:26]=[C:25]([S:22]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)(=[O:23])=[O:24])[CH:33]=2)[CH:29]=[CH:1]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 86602625HCID 86602625, 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-b1cf8ef0c71e4d20aecb64b6827fc1c4
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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