Methanol → HCID 13853732, compound

HRID 979306Notes

Reaction equation

HRID 979306 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:7]([S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:17][CH3:18])[CH:10]=3)=[CH:6][C:5](=[O:19])[CH:4]=1.[Cl:20]Cl.CO>C(O)(=O)C>[Cl:20][C:6]1[C:5](=[O:19])[CH:4]=[C:3]([O:2][CH3:1])[C:16]2[C:7]=1[S:8][C:9]1[C:14](=[CH:13][CH:12]=[C:11]([O:17][CH3:18])[CH:10]=1)[N:15]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 24526ChlorineHCID 12199928HCID 12199928, compound

Product 1

HCID 13853732HCID 13853732, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a suspension of 1,7-dimethoxy-3H-phenothiazin-3-one (800 mg) in acetic acid (24 ml) was added a 1.15M solution of Cl2 in acetic acid (3.1 ml). After 15 minutes, methanol was added and the mixture was filtered, washed with ether and air dried to afford a mixture of the two title compounds (700 mg), which were separated on a silica gel column (EtOAc:CH2Cl2, 1:9), affording 4-chloro-1,7-dimethoxy-3H-phenothiazin-3-one, m.p. 278°-280° C. (dec.)

Workup

  1. filtrationthe mixture was filtered
  2. washwashed with ether and air
  3. customdried
  4. customto afford
  5. customwere separated on a silica gel column (EtOAc:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-57720514376b4be092ba516afa07f31f
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

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