Thioglycolic Acid → HCID 15981241, compound

HRID 271184Notes

Reaction equation

HRID 271184 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[C:22](C(O)=O)=[N:21]2)[CH:5]=[C:6]([Cl:19])[C:7]=1[CH2:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[NH:11][N:10]=1.SCC(O)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH:22]=[N:21]2)[CH:5]=[C:6]([Cl:19])[C:7]=1[CH2:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[NH:11][N:10]=1

Participants

4

Reactant 2

HCID 1133Thioglycolic AcidHCID 59834546HCID 59834546, compound

Product 1

HCID 15981241HCID 15981241, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

2-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (49) (101.5 mg, 0.224 mmol) was treated with mercaptoacetic acid (2.2 mL). The reaction mixture was stirred with a magnetic stirrer and was heated to 155° C. for 24 h. The reaction mixture was then cooled to room temperature, diluted with water (25 mL) and extracted with ethyl acetate (25 mL). The organic layer was separated and washed with a 1N aqueous sodium hydroxide solution (3×10 mL). The aqueous layers were combined and acidified to pH=4. The resulting solids were filtered and rinsed well with water followed by petroleum ether. The solids were dried under vacuum to afford dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-[1,2,4]triazine-3,5-dione (50) (36 mg, 40%) as a tan solid; EI(+)-HRMS m/z calcd for C17H15Cl2N5O3 (M+H)1+ 408.0625, found 408.0626. Molecular Weight=408.2468; Exact Mass=407.0552

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate (25 mL)
  3. customThe organic layer was separated
  4. washwashed with a 1N aqueous sodium hydroxide solution (3×10 mL)
  5. filtrationThe resulting solids were filtered
  6. washrinsed well with water
  7. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-f99510d172ef4231ab2af4d134fb6d8c
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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