Phosphorus oxide (P4O10) → 7-Mercapto-4-methylcoumarin

HRID 1681119Notes

Reaction equation

HRID 1681119 reaction equation
CN(C)C(=O)[S:4][C:5]1[CH:16]=[CH:15][C:8]2[C:9]([CH3:14])=[CH:10][C:11](=[O:13])[O:12][C:7]=2[CH:6]=1.C[O-].[Na+].C(OCC)(=O)C.C1(C)C=CC=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>CO>[SH:4][C:5]1[CH:16]=[CH:15][C:8]2[C:9]([CH3:14])=[CH:10][C:11](=[O:13])[O:12][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 14812Phosphorus oxide (P4O10)HCID 395497HCID 395497, compoundHCID 10942334Sodium MethoxideHCID 21584019Toluene ethylacetate

Product 1

HCID 46908187-Mercapto-4-methylcoumarinYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

26.3 g (0.1 mol) of S-(4-methyl-2-oxo-2H-1-benzopyran-7-yl) dimethylthiocarbamate are suspended in 300 ml of methanol under a nitrogen atmosphere. 0.2 mol of sodium methylate (8% solution of Na (w/v) in methanol) is added at room temperature and the mixture is heated at 45° C. for 4 hours. The disappearance of the starting material is monitored by thin layer chromatography using an ethyl acetate/toluene mixture (1/4 v/v) as the eluent. After cooling, the reaction medium is hydrolyzed on an ice/concentrated hydrochloric acid mixture and, after stirring for 30 minutes, the precipitate obtained is filtered off and then washed with water. After drying over P2O5, 19.2 g (yield≈100%) of the expected product are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate obtained
  3. filtrationis filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-a18fda158a8b4d378ec48a13ee5c5d5c
Source dataset
uspto-grants-1992_12
Patent number
US05169838

Reaction notes

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