Methanol → 4-Bromo-2,7-dimethoxy-3H-phenothiazin-3-one

HRID 979297Notes

Reaction equation

HRID 979297 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[C:18](=[O:19])[CH:17]=[C:16]2[C:7](=[N:8][C:9]3[C:14]([S:15]2)=[CH:13][C:12]([O:20][CH3:21])=[CH:11][CH:10]=3)[CH:6]=1.CO>C(O)(=O)C>[Br:1][C:17]1[C:18](=[O:19])[C:5]([O:4][CH3:3])=[CH:6][C:7]2[C:16]=1[S:15][C:14]1[C:9](=[CH:10][CH:11]=[C:12]([O:20][CH3:21])[CH:13]=1)[N:8]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 121999232,7-dimethoxy-3H-phenothiazin-3-one

Product 1

HCID 1221824-Bromo-2,7-dimethoxy-3H-phenothiazin-3-oneYield 96.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (280 g) in acetic acid (2.8 l) was added over a period of 30 minutes to a suspension of 2,7-dimethoxy-3H-phenothiazin-3-one (250 g) (Step 3) in acetic acid (7.5 l) and stirred for 2 hours. Methanol (12 l) was added and the mixture was stirred until the black suspension became an orange suspension. Then, the precipitate was filtered, washed with methanol and air-dried to afford the desired compound (312 g), m.p. 260°-261° C.

Workup

  1. stirringthe mixture was stirred until the black suspension
  2. filtrationThen, the precipitate was filtered
  3. washwashed with methanol
  4. customair-dried

Sources & evidence

ORD record
ord-314f41547af84ba58fec20b4c4d6a924
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

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