Malonic Acid → HCID 178481360, compound

HRID 2036282Notes

Reaction equation

HRID 2036282 reaction equation
[SH:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[CH:3]=1.[C:12](O)(=[O:17])[CH2:13][C:14](O)=[O:15].C(OC(=O)C)(=O)C>C(O)(=O)C>[OH:17][C:12]1[C:3]2[C:4](=[O:11])[N:5]([CH3:10])[C:6](=[O:9])[N:7]([CH3:8])[C:2]=2[S:1][C:14](=[O:15])[CH:13]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 12297296HCID 12297296, compound

Product 1

HCID 178481360HCID 178481360, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of Step 2 intermediate (12.75 g, 74.127 mmol), malonic acid (9.30 g, 88.953 mmol), acetic acid (7.41 ml) and acetic anhydride (16.8 ml) was heated to 80° C. under nitrogen atmosphere for 2 h. The reaction mixture was cooled to room temperature and quenched with water (50 ml). Precipitated solid was filtered, washed with water (2×50 ml) and dried well to obtain 14.4 g of the product as brown solid; 1H NMR (300 MHz, DMSO-d6) δ 3.28 (s, 3H), 3.48 (s, 3H), 5.73 (s, 1H), 13.76 (br s, 1H).

Workup

  1. customquenched with water (50 ml)
  2. customPrecipitated solid
  3. filtrationwas filtered
  4. washwashed with water (2×50 ml)
  5. customdried well

Sources & evidence

ORD record
ord-6eabb014cbf9444d91b3f9327b3711fc
Source dataset
uspto-grants-2013_11
Patent number
US08575178B2

Reaction notes

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