2,4-Dimethylbenzoyl chloride → HCID 178424080, compound

HRID 868730Notes

Reaction equation

HRID 868730 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH3:6][C:7]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=1[C:9](Cl)=O>N1C=CC=CC=1>[CH3:6][C:7]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=1[C:9]1[NH:5][C:3](=[S:4])[NH:2][N:1]=1

Participants

4

Reactant 2

HCID 1408672,4-Dimethylbenzoyl chlorideHCID 2723789Thiosemicarbazide

Product 1

HCID 178424080HCID 178424080, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of thiosemicarbazide (800 mg, 8.78 mmol) in 9 mL of pyridine was added 2,4-dimethylbenzoyl chloride (1.68 g, 10 mmol). The reaction was heated at 150° C. for 10 min using a microwave synthesizer. The yellow solution was evaporated to dryness and then diluted with water. The white solid was then collected and washed with water. The solid was suspended in 20 mL of 1 M aq. NaHCO3. The suspension was heated at 180° C. for 1 h using a microwave synthesizer. Then the mixture was filtered hot and the aqueous solution was cooled in ice and acidified to pH 3 with conc. HCl. The solid was filtered and washed with water and dried to give white powder (43%).

Workup

  1. customThe yellow solution was evaporated to dryness
  2. additiondiluted with water
  3. customThe white solid was then collected
  4. washwashed with water
  5. temperatureThe suspension was heated at 180° C. for 1 h
  6. filtrationThen the mixture was filtered hot
  7. temperaturethe aqueous solution was cooled in ice
  8. filtrationThe solid was filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-7b816204faee40d0930c864cecfd8108
Source dataset
uspto-grants-2015_03
Patent number
US08968708B2

Reaction notes

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