Dimethylformamide → HCID 178495924, compound

HRID 2405688Notes

Reaction equation

HRID 2405688 reaction equation
[I-:1].[I-].[I-].[NH2:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[S+:16][C:15]1[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=1)[N:9]=2.NC1C=CC2C(C=1)=[S+][C:30]1[C:25](=CC=[CH:28][CH:29]=1)[N:24]=2.NC1C=CC2[C:47]([CH:48]=1)=[S+]C1C(=CC=CC=1)N=2.[C:49]([O-:52])([O-])=O.[Cs+].[Cs+].N1[CH2:59][CH2:58]CC1.CN([CH:63]=[O:64])C>>[I-:1].[CH3:63][O:64][CH2:58][CH2:59][N:4]([CH2:47][CH2:48][O:52][CH3:49])[C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[S+:16][C:15]1[C:10](=[CH:11][CH:12]=[C:13]([N:24]3[CH2:25][CH2:30][CH2:29][CH2:28]3)[CH:14]=1)[N:9]=2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 178507328HCID 178507328, compound

Product 1

HCID 178495924HCID 178495924, compound

Procedure

The 3-aminophenothiazin-5-ium triiodide was dissolved in DMF (40 mL) and Cs2CO3 was added followed by pyrrolidine (3 mL, 3 mmol). The resulting reaction mixture was stirred rapidly at room temperature for 48 h. The solvent was evaporated and the residue was dissolved in a 3:1 mixture of CHCl3/MeOH. The mixture was filtered and the solvent evaporated to give a residue, which was purified by flash silica gel chromatography to give a dark solid.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in a 3:1 mixture of CHCl3/MeOH
  4. filtrationThe mixture was filtered
  5. customthe solvent evaporated
  6. customto give a residue, which
  7. customwas purified by flash silica gel chromatography
  8. customto give a dark solid

Sources & evidence

ORD record
ord-7be6b6a2a83c4bef980f397375f51a0d
Source dataset
uspto-grants-2014_08
Patent number
US08809317B2

Reaction notes

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