Sodium methanethiolate → HCID 10936102, compound

HRID 719175Notes

Reaction equation

HRID 719175 reaction equation
F[C:2]1[C:7]2=[CH:8][CH:9]=[C:10]3[C:19]([N:18]=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[C:16]4[C:20]([OH:22])=[O:21])=[N:11]3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:23][S-:24].[Na+]>CS(C)=O>[CH3:23][S:24][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]3[C:19]([N:18]=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[C:16]4[C:20]([OH:22])=[O:21])=[N:11]3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 10989968HCID 10989968, compound

Product 1

HCID 10936102HCID 10936102, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of 4-fluoro-benzo[a]phenazine-11-carboxylic acid (II.3, see Reference Example 1B (58 mg) in dry DMSO (3 mL) was added sodium thiomethoxide (55 mg) and the reaction mixture heated at 100° C. for 1.5 hours and 130° C. for 1 hour. The reaction mixture was then cooled to room temperature, quenched with acetic acid, extracted with ethyl acetate, washed with water, dried and the solvent removed in vacuo to yield the title compound as a red solid (37 mg).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customquenched with acetic acid
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-96c5c8c5df5a41789c33059bf6b27c1c
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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