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Methyl iodide → HCID 13712494, compound

HRID 64969
Notes
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Reaction equation

HRID 64969 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=12.CI.[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:22][O:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 137124785-hydroxy-12H-benzo[a]phenothiazine

Product 1

HCID 13712494HCID 13712494, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of 5-hydroxy-12H-benzo[a]phenothiazine (2.65 g) and methyl iodide (2.5 ml) in DMF (dimethylformamide) (10 ml) there was added powdered potassium carbonate (2.0 g). The mixture was stirred at room temperature and after 15 minutes, another addition of potassium carbonate (2.0 g) and methyl iodide (2.0 ml) was done. The mixture was stirred for a further 20 minutes, then it was diluted with ethyl acetate (100 ml and washed with water (60 ml) twice, dried and evaporated down. The residue was triturated with ether to afford solid crude product which was filtered (1.7 g). This crude product was chromatographed on a column of silica gel, eluting with dichloromethane to afford pure title compound (1.33 g), m.p. 168°-170° C.

Workup

  1. stirringThe mixture was stirred for a further 20 minutes
  2. washwashed with water (60 ml) twice
  3. customdried
  4. customevaporated down
  5. customThe residue was triturated with ether
  6. customto afford solid crude product which
  7. filtrationwas filtered (1.7 g)
  8. customThis crude product was chromatographed on a column of silica gel
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-c801a09080ee4a9b9ed80e4efb6baf6f
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04611056

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes