Triethylamine → HCID 13589046, compound

HRID 1195052Notes

Reaction equation

HRID 1195052 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:14]/[O:15][CH2:16][C:17]#[N:18])/[C:8]([O:10]CC=C)=[O:9])[N:6]=1.C(N(CC)CC)C>C(OCC)(=O)C.[Pd](Cl)Cl.P(OCC)(OCC)(OCC)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:14]/[O:15][CH2:16][C:17]#[N:18])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 88629724HCID 88629724, compound

Product 1

HCID 13589046HCID 13589046, compoundYield 54.8%

Reagents, catalysts & solvents 3

HCID 6535Triethyl PhosphateCatalystHCID 24290Palladium ChlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.66 g (0.01 mol) of allyl 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetate in 100 ml of ethyl acetate are treated while stirring with 17.73 mg (0.0001 mol) of palladium chloride and 0.083 ml (0.0005 mol) of triethyl phosphate. After the addition of 1.54 ml (0.011 mol) of triethylamine, the mixture is stirred at room temperature for 24 hours. Crude 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetic acid triethylamine salt precipitates out. The filtered-off crude salt (2.9 g) is dissolved in 30 ml of methanol. The solution is adjusted to pH 3 with 2N aqueous hydrochloric acid. Crystallization occurs. The crystals obtained are filtered off and washed with methanol and ether. There are obtained 1.24 g (51.2%) of 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetic acid of melting point 140°-142° C. (decomposition).

Workup

  1. customCrude 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetic acid triethylamine salt precipitates out
  2. dissolutionThe filtered-off crude salt (2.9 g) is dissolved in 30 ml of methanol
  3. customCrystallization
  4. customThe crystals obtained
  5. filtrationare filtered off
  6. washwashed with methanol and ether

Sources & evidence

ORD record
ord-f497880b1b0245df8fec6963167322dd
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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