Dimethylformamide → 4-chloro-3-methoxy-10-methyl-10H-phenothiazine

HRID 231044Notes

Reaction equation

HRID 231044 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].[CH3:6]I.[Cl:8][C:9]1[C:22]2[S:21][C:20]3C(=[CH:16][CH:17]=[CH:18][CH:19]=3)NC=2[CH:12]=[CH:11][C:10]=1[OH:23].[H-].[Na+]>CO>[Cl:8][C:9]1[C:22]2[S:21][C:20]3[C:3](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:2]([CH3:1])[C:4]=2[CH:12]=[CH:11][C:10]=1[O:23][CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 98814184-chloro-3-hydroxy-10H-phenothiazine

Product 1

HCID 138820274-chloro-3-methoxy-10-methyl-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 25 ml of DMF was added methyl iodide (2.9 ml), 4-chloro-3-hydroxy-10H-phenothiazine (see Example 3) (2.3 g) and sodium hydride (0.672 g). The resulting reaction mixture was stirred at ambient temperature for 12 hours. At 0° C., MeOH was added to destroy the remaining hydride, then H2O. The resulting solution was extracted with ethyl acetate and the organic phase, dried and evaporated. The resulting residue was then purified by chromatography on silica gel to give 1.5 g of 4-chloro-3-methoxy-10-methyl-10H-phenothiazine (m.p.: 136° C.).

Workup

  1. customThe resulting reaction mixture
  2. customto destroy the remaining hydride
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. customthe organic phase, dried
  5. customevaporated
  6. customThe resulting residue was then purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3ca45229dee74b15b5ff8be4ddb772df
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

Loading…