Methyl iodide → HCID 13882037, compound

HRID 231059Notes

Reaction equation

HRID 231059 reaction equation
[C:1]([O:4][C:5]1[C:6]([O:22][CH3:23])=[CH:7][C:8]2[NH:9][C:10]3[C:15]([S:16][C:17]=2[C:18]=1[Br:19])=[CH:14][C:13]([O:20][CH3:21])=[CH:12][CH:11]=3)(=[O:3])[CH3:2].CI.[CH3:26]C(C)([O-])C.[K+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:6]([O:22][CH3:23])=[CH:7][C:8]2[N:9]([CH3:26])[C:10]3[C:15]([S:16][C:17]=2[C:18]=1[Br:19])=[CH:14][C:13]([O:20][CH3:21])=[CH:12][CH:11]=3)(=[O:3])[CH3:2].[Br:19][C:18]1[C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:20][CH3:21])[CH:14]=3)[N:9]([CH3:26])[C:8]=2[CH:7]=[C:6]([O:22][CH3:23])[C:5]=1[O:4][CH3:1]

Participants

7

Reactant 3

HCID 6328Methyl iodide2×HCID 13853739HCID 13853739, compoundHCID 23665647Potassium tert-butoxide2×

Product 2

HCID 13882037HCID 13882037, compoundHCID 13882040HCID 13882040, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-acetoxy-4-bromo-2,7-dimethoxy-10H-phenothiazine (8.0 g) in N,N-dimethylformamide (80 ml) there was added at room temperature methyl iodide (16 ml) and then potassium t-butoxide (3 g). The mixture was stirred at room temperature. Over a period of 24 hours, seven further additions of methyl iodide (10 ml) and potassium t-butoxide (2 g) were made. The final reaction mixture was diluted with ethyl acetate and the solids filtered. The filtrate was washed three times with brine, dried and evaporated. Flash chromatography of the residue on a column of silica gel, eluting with a 1:9 mixture of ethyl acetate and hexane afforded 3-acetoxy-4-bromo-2,7-dimethoxy-10-methyl-10H-phenothiazine (830 mg, m.p. 189°-190° C.) and 4-bromo-10-methyl-2,3,7-trimethoxy-10H-phenothiazine (2.86 g, m.p. 135°-137° C.).

Workup

  1. customThe final reaction mixture
  2. filtrationthe solids filtered
  3. washThe filtrate was washed three times with brine
  4. customdried
  5. customevaporated
  6. washFlash chromatography of the residue on a column of silica gel, eluting with a 1:9 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b5a6abd804a74b7e8c9839d368b509c6
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

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