Diethyl Ether → 2-methoxy-10H-phenothiazine-1-carbaldehyde

HRID 393520Notes

Reaction equation

HRID 393520 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=1.[CH2:17]([O:19]CC)C.[Li]CCCC.CN(C=O)C>CCCCCC.O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[C:4]=1[CH:17]=[O:19]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 74490Methyl phenothiazin-2-yl etherHCID 178418339Butyllithium

Product 1

HCID 226464282-methoxy-10H-phenothiazine-1-carbaldehydeYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

4.6 g (20 mmol) of 2-methoxy-10H-phenothiazine are dissolved, under an argon atmosphere, in a three-necked flask, containing 140 ml anhydrous ethyl ether. 20 ml (50 mmol) of a solution of nBuLi (2.5 M) in hexane is then added dropwise, at 20° C. The reaction mixture is agitated for 3 hours at 20° C. before the dropwise addition of 6.2 ml (80 mmol) of anhydrous DMF. Agitation is maintained for another 15 hours at 20° C. The whole is then poured into 150 ml ice-cooled water and the product is extracted twice using 200 ml of ethyl acetate. The organic solution is washed with 100 ml of salt water, dried over MgSO4, filtered and concentrated under vacuum. The evaporation residue is taken up in diisopropyl ether, filtered and dried to produce a red solid with a yield of 30%. Melting point: 155-160° C.

Workup

  1. extractionthe product is extracted twice
  2. washThe organic solution is washed with 100 ml of salt water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. filtrationfiltered
  7. customdried
  8. customto produce a red solid with a yield of 30%

Sources & evidence

ORD record
ord-27b44ed0476c4c9bb0dc456a9c67c7b7
Source dataset
uspto-grants-2004_10
Patent number
US06809090B2

Reaction notes

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