3-Nitrobenzaldehyde → HCID 178503557, compound

HRID 1766066Notes

Reaction equation

HRID 1766066 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[N+:11]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([O-:13])=[O:12].[C:22]([CH2:24][C:25](OCC)=[O:26])#[N:23].C(=O)([O-])[O-].[K+].[K+]>CCO>[C:22]([C:24]1[C:17]([C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=2)=[N:10][C:8]([S:7][CH3:6])=[N:9][C:25]=1[OH:26])#[N:23]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 178503557HCID 178503557, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of S-methylisothiourea sulfate (69.0 g), 3-nitrobenzaldehyde (75.0 g), ethyl cyanoacetate (56.0 ml) and potassium carbonate (72.5 g) in abs. EtOH (1500 ml) was stirred at 60° C. for 16 h. The reaction mixture was cooled to 0° C. in an ice bath. The resulting precipitate was filtered off, washed with abs. EtOH and dissolved in hot water (100° C.). The solution was cooled to room temperature, acidified with 2N HCl to pH 2 and cooled to 0° C. in an ice bath. The resulting precipitate was filtered off and washed with ice water. Residual water in the precipitate was removed by coevaporation with 1,4-dioxane.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with abs
  3. dissolutionEtOH and dissolved in hot water (100° C.)
  4. temperatureThe solution was cooled to room temperature
  5. temperaturecooled to 0° C. in an ice bath
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with ice water
  8. customResidual water in the precipitate was removed by coevaporation with 1,4-dioxane

Sources & evidence

ORD record
ord-79d8b1939d38421ca2a4f25058d0ae19
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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