Hydrazine hydrate (1:1) → HCID 14010096, compound

HRID 1788787Notes

Reaction equation

HRID 1788787 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][C:13](=[CH2:30])[C:14]([O:16][CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].O.NN>C(Cl)Cl.C(O)C>[NH2:3][O:12][C:13](=[CH2:30])[C:14]([O:16][CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14010095HCID 14010095, compound

Product 1

HCID 14010096HCID 14010096, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(1,3-dioxo-2H-isoindol-2-yl)oxy]-2-propenoic acid, diphenylmethyl ester (6.07 g, 15.2 mmole) in 375 ml of methylene chloride under argon at 0° C. was added hydrazine hydrate (0.76 g, 15.2 mmole) in 4 ml absolute ethanol. After one hour at 0° C., the mixture was evaporated to dryness at +10° C. and triturated with ethyl ether. Filtration and concentration of the filtrates gave 2-aminooxy-2-propenoic acid, diphenylmethyl ester as a residue. This compound was then treated at 20° C. with a solution of 2-amino-4-thiazoleglyoxylic acid (2.61 g, 15.2 mmole) in dimethylformamide (50 ml), followed by 5 ml of water. The reaction was stirred at 20° C. for 20 hours, and was then chilled and diluted with 250 ml of water. Stirring of the resulting gum gave a granular solid which was filtered, washed with water, and then azeotroped with acetonitrile to dryness. The dry solid was slurried with 100 ml of acetonitrile, filtered, and finally washed sequentially with acetonitrile, ethyl ether, and hexane. Drying in air gave 1.97 g of the title compound.

Workup

  1. customthe mixture was evaporated to dryness at +10° C.
  2. customtriturated with ethyl ether
  3. filtrationFiltration and concentration of the filtrates

Sources & evidence

ORD record
ord-81a98eb62d3a4e8db0a1240526ed7b45
Source dataset
uspto-grants-1987_08
Patent number
US04684722

Reaction notes

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