Diethyl Ether → 5-Methoxymethoxy-12H-benzo[a]phenothiazine

HRID 2352221Notes

Reaction equation

HRID 2352221 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:17]=[C:16]2[C:7]([NH:8][C:9]3[C:14]([S:15]2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=12.[CH3:22][O:23][CH2:24]Cl.C(OCC)C>C1COCC1.O>[CH3:22][O:23][CH2:24][O:3][C:4]1[CH:17]=[C:16]2[C:7]([NH:8][C:9]3[C:14]([S:15]2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=12

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 137124785-hydroxy-12H-benzo[a]phenothiazine

Product 1

HCID 137124925-Methoxymethoxy-12H-benzo[a]phenothiazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (75 mg) was added to a solution of 5-hydroxy-12H-benzo[a]phenothiazine (1) (500 mg) and chloromethyl methyl ether (154 mg) in THF (10 ml) and the reaction mixture was stirred for 15 minutes. Diethyl ether (60 ml) was added to the reaction mixture followed by water (60 ml). The ether layer was decanted, dried and evaporated to dryness. The resulting residue was chromatographed on silica gel (CH2Cl1 /hexane (7:3)) to afford the title compound, m.p. 103° C. Anal. C18H15NO2S; Calcd.: C, 69.87; H, 4.89; N, 4.53; S, 10.36. Found: C, 69.75; H, 5.01; N, 4.41; S, 10.53.

Workup

  1. customThe ether layer was decanted
  2. customdried
  3. customevaporated to dryness
  4. customThe resulting residue was chromatographed on silica gel (CH2Cl1 /hexane (7:3))

Sources & evidence

ORD record
ord-4c13011c57fa4fb2ba5f2bb13b5e1763
Source dataset
uspto-grants-1989_10
Patent number
US04876246

Reaction notes

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