Hexane → 4-Bromo-7-methoxy-2-(4-methylpiperazin-1-yl)-3H-phenothiazin-3-one

HRID 979308Notes

Reaction equation

HRID 979308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]1[C:7](=[CH:8][C:9](=[O:24])[C:10]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:11]1)[S:6]2.[Br:25]Br.CCCCCC>C(O)(=O)C>[Br:25][C:8]1[C:9](=[O:24])[C:10]([N:17]2[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]2)=[CH:11][C:12]2[C:7]=1[S:6][C:5]1[C:14](=[CH:15][CH:16]=[C:3]([O:2][CH3:1])[CH:4]=1)[N:13]=2

Participants

5

Reactant 3

HCID 8058HexaneHCID 24408BromineHCID 138537347-Methoxy-2-(4-methylpiperazin-1-yl)-3H-phenothiazine-3-one

Product 1

HCID 138537354-Bromo-7-methoxy-2-(4-methylpiperazin-1-yl)-3H-phenothiazin-3-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a suspension of 7-methoxy-2-(4-methylpiperazin-1-yl)-3H-phenothiazin-3-one (500 mg) in acetic acid (10 ml) was added a solution of bromine in acetic acid (0.5M) (6 ml) and stirred for 5 minutes. Hexane (100 ml) was added and the resulting precipitate was filtered. The solid was suspended in a mixture of aqueous K2CO3 (50 ml), EtOAc (100 ml) and methanol (20 ml) and stirred for 15 minutes. After filtration and decantation, the organic layer was washed with brine, dried and evaporated to dryness to afford the title compound (190 mg) m.p. 209°-210° (dec.).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. additionThe solid was suspended in a mixture of aqueous K2CO3 (50 ml), EtOAc (100 ml) and methanol (20 ml)
  3. stirringstirred for 15 minutes
  4. filtrationAfter filtration and decantation
  5. washthe organic layer was washed with brine
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-83c87d3c314b4c51a44c41ab61e687ff
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

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