Carbon Disulfide → HCID 53357108, compound

HRID 448171Notes

Reaction equation

HRID 448171 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:25])[C:8]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)=[C:9]([S:13][CH3:14])[O:10]2)=[CH:5][CH:4]=1.C(=S)=S.[H-].[Na+]>CN(C=O)C.O>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:25])[C:8]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)=[C:9]([S:13][CH3:14])[O:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 67367114HCID 67367114, compound

Product 1

HCID 53357108HCID 53357108, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Synthesis: Step 1: Synthesis of methyl 4-(7-methoxy-2-(methylthio)-4-oxo-4H-chromen-3-yl)benzoate. A stirred mixture of Intermediate B (100 mg, 0.33 mmol) and carbon disulfide (127 mg, 1.67 mmol) in DMF (5.0 mL) was cooled to 0° C. and NaH (24 mg, 1.0 mmol) was added. The reaction mixture was stirred at 0 ° C. for 30 min. Then Mel (94 mg, 0.67 mmol) was added and the reaction mixture was stirred at room temperature for 3 h. The solution was diluted with water (10 mL), extracted with DCM (50 mL×3). The organic layers were dried over Na2SO4, concentrated and purified by silica gel column chromatography (PE:EA=3:1) to afford product (36 mg (not pure), 30%). MS (ESI): m/z 357.0 [M+1]+.

Workup

  1. customSynthesis
  2. additionThen Mel (94 mg, 0.67 mmol) was added
  3. stirringthe reaction mixture was stirred at room temperature for 3 h
  4. extractionextracted with DCM (50 mL×3)
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (PE:EA=3:1)
  8. customto afford product (36 mg (not pure), 30%)

Sources & evidence

ORD record
ord-37fbcb1cb97541ca95424daede113e96
Source dataset
uspto-grants-2013_07
Patent number
US08481590B2

Reaction notes

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