Water → 4-chloro-3-isobutyryloxy-10-methyl-10H-phenothiazine

HRID 979081Notes

Reaction equation

HRID 979081 reaction equation
[Cl:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19].[CH3:22]I.[H-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH3:22])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:16][C:17](=[O:21])[CH:18]([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 138820304-chloro-3-isobutyryloxy-10H-phenothiazine

Product 1

HCID 138820314-chloro-3-isobutyryloxy-10-methyl-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-3-isobutyryloxy-10H-phenothiazine (see Example 8) (202 mg) in DMF (5 ml) was added methyl iodide (0.2 ml) and sodium hydride (18 mg) at 0° C. The reaction mixture was stirred at ambient temperature for 12 hours. To the reaction mixture was added water and the resulting aqueous layer extracted with EtOAc. The organic layers were collected, dried and evaporated to give a residue which was purified by chromatography on silica gel (plates) to give 100 mg of 4-chloro-3-isobutyryloxy-10-methyl-10H-phenothiazine (m.p. 147° C.).

Workup

  1. extractionthe resulting aqueous layer extracted with EtOAc
  2. customThe organic layers were collected
  3. customdried
  4. customevaporated
  5. customto give a residue which
  6. customwas purified by chromatography on silica gel (plates)

Sources & evidence

ORD record
ord-50315082fcfb46d1bbc3c5fa362617f2
Source dataset
uspto-grants-1987_05
Patent number
US04666907

Reaction notes

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