HCID 22341328, compound → HCID 11579867, compound

HRID 1767572Notes

Reaction equation

HRID 1767572 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:16](=[O:17])[NH:15][C:14](=[O:18])[C:13](C(O)=O)=[N:12]2)[CH:7]=[CH:8][C:9]=1[Cl:10])([OH:3])=[O:2]>SCC(O)=O>[Cl:10][C:9]1[CH:8]=[CH:7][C:6]([N:11]2[C:16](=[O:17])[NH:15][C:14](=[O:18])[CH:13]=[N:12]2)=[CH:5][C:4]=1[C:1]([OH:3])=[O:2]

Participants

3

Reactant 1

HCID 22341328HCID 22341328, compound

Product 1

HCID 11579867HCID 11579867, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 1133Thioglycolic AcidSolvent

Conditions

Temperature
175 °C

Procedure

A suspension of 2-(3-carboxy-4-chloro-phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (3.4 g) in mercaptoacetic acid (2 ml) was stirred at 175° C. After 20 h the resulting solution was cooled to room temperature during which time a precipitate formed. The mixture was dumped into ice-water, stirred for 30 minutes and filtered to give a yellow solid. The solid was dried under vacuum for 24 hours to give 2.1 g of the title intermediate. Mass spectrum [M−1] 3:1 ratio of 266.1 and 268.1; 1H nmr (500 MHz, CD3OD) δ 7.58 (s, 1H), 7.60 (d, J=8.8 Hz, 1H), 7.72 (dd, J=2.6 and 8.8 Hz), 8.09 (d, J=2.6 Hz).

Workup

  1. temperatureAfter 20 h the resulting solution was cooled to room temperature during which time a precipitate
  2. customformed
  3. stirringstirred for 30 minutes
  4. filtrationfiltered
  5. customto give a yellow solid
  6. customThe solid was dried under vacuum for 24 hours

Sources & evidence

ORD record
ord-8e0afe7cb5584e13961956f8b4efc1d1
Source dataset
uspto-grants-2007_06
Patent number
US07235549B2

Reaction notes

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