Ethyl Acetate → HCID 178513168, compound

HRID 1491882Notes

Reaction equation

HRID 1491882 reaction equation
[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([NH:18][NH2:19])=[O:17])[N:11]=2)[N:9]=1)[NH2:3].S(O)(O)(=O)=O.CS[C:27](=[NH:29])[NH2:28].C(OCC)(=O)C>CS(C)=O>[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:17])[NH:18][NH:19][C:27]([NH2:29])=[NH:28])[N:11]=2)[N:9]=1)[NH2:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 752702-Methyl-2-thiopseudourea sulfateHCID 18953851HCID 18953851, compound

Product 1

HCID 178513168HCID 178513168, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(diaminomethyleneamino)-4-(6-hydrazinocarbonylpyridin-2-yl)thiazole (3.0 g) and 2-methyl-2-thiopseudourea sulfate (1.8 g) in dimethylsulfoxide (30 ml) was stirred for 6 hours at 100° C., and then the mixture was cooled to ambient temperature. To the mixture was added ethyl acetate (30 ml) under stirring. The isolated precipitate was collected by filtration and the precipitate was added to a mixture of water and ethyl acetate. The mixture was adjusted to pH 10 with 4N-sodium hydroxide and precipitate was collected by filtration to give 2-(diaminomethyleneamino)-4-(6-guanidinocarbamoylpyridin-2-yl)thiazole (2.48 g).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. stirringunder stirring
  3. filtrationThe isolated precipitate was collected by filtration
  4. additionthe precipitate was added to a mixture of water and ethyl acetate
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-6c58ff3380a349e39c454132c3300a1c
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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