Water → HCID 14031257, compound

HRID 247375

Reaction equation

HRID 247375 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:17]1([CH:23](Cl)[CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O>[C:17]1([CH:23]([N:13]2[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[O:6][C:7]3[C:12]2=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12648(1-Chloroethyl)benzeneHCID 24758Sodium hydrideHCID 67278Phenoxazine

Product 1

HCID 14031257HCID 14031257, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of phenoxazine 76 g, 0.417 mol (Aldrich Chemical Co., Milwaukee, WI, Cat. No. P1,585-8) in dry dimethylformamide (120 ml) was added to a stirred suspension of sodium hydride (22 g, 0.458 mol, 50% suspension in mineral oil) in dry dimethylformamide (500 ml). After 1 hour at room temperature α-phenylethyl chloride (59 g, 0.43 mol) was added dropwise and when the addition was completed, stirring was continued for another 30 min. The solution was poured into water, the product extracted with ethyl acetate, the extract washed with water, and dried over sodium sulfate. The solvent was removed under reduced pressure. N-α-Phenylethylphenoxazine was crystallized from ether-hexane, mp 100° C.

Workup

  1. additionwhen the addition
  2. extractionthe product extracted with ethyl acetate
  3. washthe extract washed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customN-α-Phenylethylphenoxazine was crystallized from ether-hexane, mp 100° C.

Sources & evidence

ORD record
ord-f3b6d518f76f4e13a3e66dde83eec807
Source dataset
uspto-grants-1987_11
Patent number
US04707473

Linked notes

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