Sulfuric Acid → HCID 11469739, compound

HRID 747832Notes

Reaction equation

HRID 747832 reaction equation
[OH-].[K+].C[NH:4][C:5](=[NH:7])S.OS(O)(=O)=O.[CH3:13][C:14]1[CH:27]=[CH:26][C:17]([C:18]([CH2:20][C:21](OCC)=[O:22])=[O:19])=[CH:16][CH:15]=1>O>[NH2:7][C:5]1[O:19][C:18]([C:17]2[CH:26]=[CH:27][C:14]([CH3:13])=[CH:15][CH:16]=2)=[CH:20][C:21](=[O:22])[N:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 292637Ethyl 3-(4-methylphenyl)-3-oxopropanoateHCID 178485201HCID 178485201, compound

Product 1

HCID 11469739HCID 11469739, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium hydroxide (12.55 g, 224 mmol) was added to the vigorously stirred solution of methylthiopseudourea.H2SO4 (14.57 g, 52 mmol) in water (80 ml). Ethyl (4-methyl)benzoylacetate (20.0 g, 97 mmol) (obtained in preparation 1) was added to it and stirred at room temperature for 18 hours. The solid thus obtained was filtered, washed with water, ether and dried at 60° C. in vacuum to yield the title compound (1.85 g, 9.5%). 1H-NMR (DMSO-d6): δ 2.37 (s, 3H), 6.46 (s, 1H), 7.33-7.35 (d, 2H), 7.76-7.78 (d, 2H), 7.91 (bs, 2H, D2O exchangeable). MS m/z: 203.1 (M+).

Workup

  1. customThe solid thus obtained
  2. filtrationwas filtered
  3. washwashed with water, ether
  4. customdried at 60° C. in vacuum

Sources & evidence

ORD record
ord-e115c6f11c6443c69421bcefd19cf84f
Source dataset
uspto-grants-2008_07
Patent number
US07399760B2

Reaction notes

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