Glyoxylic acid, monohydrate → Hwa 131

HRID 1165133Notes

Reaction equation

HRID 1165133 reaction equation
O.[C:2]([OH:6])(=O)[CH:3]=O.Br.[NH2:8][C:9]1[S:10][CH2:11][C:12]([C:15]2[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([OH:25])=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:16]=2)=[N:13][N:14]=1>O.C(O)(=O)C.Cl>[C:26]([C:17]1[CH:16]=[C:15]([C:12]2[N:14]3[N:13]=[CH:3][C:2](=[O:6])[N:8]=[C:9]3[S:10][CH:11]=2)[CH:20]=[C:19]([C:21]([CH3:24])([CH3:22])[CH3:23])[C:18]=1[OH:25])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 2

HCID 15620607Glyoxylic acid, monohydrateHCID 136364585HCID 136364585, compound

Product 1

HCID 159492Hwa 131

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4.8 g (0.05 mol) of glyoxylic acid monohydrate in 75 ml of water were added dropwise to a solution of 10.0 g (0.025 mol) of 2-amino-5-(3,5-di-tert.butyl-4-hydroxyphenyl)-6H-1,3,4-thiadiazine hydrobromide from step (c1) in 250 ml of glacial acetic acid and 25 ml of 4N hydrochloric acid at 80° C. After the mixture had been stirred at 80° C. for 20 hours, it was evaporated under reduced pressure. It was advantageously possible to purify the solid residue by column chromatography on silica gel using methylene chloride/methanol (25:1) as the eluent and subsequent recrystallization from ethanol, and, from analytical and spectroscopic investigations, the product proved to be identical to that prepared by procedures (a) and (b).

Workup

  1. customit was evaporated under reduced pressure
  2. customto purify the solid residue by column chromatography on silica gel
  3. customas the eluent and subsequent recrystallization from ethanol
  4. customthat prepared by procedures (a) and (b)

Sources & evidence

ORD record
ord-bddf200e56554c92af1d877521486423
Source dataset
uspto-grants-1990_03
Patent number
US04908364

Reaction notes

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