Methyl iodide → HCID 13853737, compound

HRID 979301Notes

Reaction equation

HRID 979301 reaction equation
[CH3:1]C(C)([O-])C.[K+].[OH:7][C:8]1[C:13]2[C:14]3[C:23](=[C:24]([CH3:27])[C:25](=[O:26])[C:12]=2[CH:11]=[CH:10][CH:9]=1)[S:22][C:21]1[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[N:15]=3.CI.CCOC(C)=O>CN(C=O)C.O>[CH3:1][O:7][C:8]1[C:13]2[C:14]3[C:23](=[C:24]([CH3:27])[C:25](=[O:26])[C:12]=2[CH:11]=[CH:10][CH:9]=1)[S:22][C:21]1[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[N:15]=3

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 135626448HCID 135626448, compound

Product 1

HCID 13853737HCID 13853737, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium tert.-butoxide (500 mg) was added to a suspension of 1-hydroxy-6-methyl-5H-benzo[a]phenothiazin-5-one (from Example 32) (500 mg) and methyl iodide (2 ml) in DMF (20 ml). After 30 minutes at room temperature, EtOAc (250 ml) was added followed by water (200 ml). The aqueous layer was decanted and the organic layer was dried and evaporated to dryness. The residue was treated with ether, filtered and air-dried to afford the desired product (420 mg), m.p. 170°-171° C.

Workup

  1. customThe aqueous layer was decanted
  2. customthe organic layer was dried
  3. customevaporated to dryness
  4. additionThe residue was treated with ether
  5. filtrationfiltered
  6. customair-dried

Sources & evidence

ORD record
ord-2da608feb8fc4a22a113e9f1b9e1060e
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

Loading…