Benzoyl chloride → N-(6-Ethoxypyridin-3-yl)thiourea

HRID 1759541Notes

Reaction equation

HRID 1759541 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH3:10])=[CH:6][CH:7]=1.[S-:11][C:12]#[N:13].[K+].C(Cl)(=O)C1C=CC=CC=1>CC(C)=O>[CH2:9]([O:8][C:5]1[N:4]=[CH:3][C:2]([NH:1][C:12]([NH2:13])=[S:11])=[CH:7][CH:6]=1)[CH3:10]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516872Potassium thiocyanateHCID 30403016-Ethoxypyridin-3-amine

Product 1

HCID 13041554N-(6-Ethoxypyridin-3-yl)thiourea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 12 g of 3-amino-6-ethoxypyridine in 30 ml of acetone was admixed with a solution of 7.6 g of potassium thiocyanate in 60 ml of acetone, and under stirring, 15.4 g of benzoyl chloride was added dropwise. The mixture was then boiled for 10 minutes. The reaction mixture was poured into ice-water and the resulting crystals (m.p. 130°-133° C.) were recovered by filtration and boiled with 50 ml of 10% sodium hydroxide for 15 minutes. After cooling, crystals (m.p. 142°-146° C.) of 6-ethoxy-3-pyridylthiourea were obtained. These crystals were dissolved in 150 ml of hot 10% potassium hydroxide, and after addition of 37 g of lead acetate, the mixture was stirred at 80° C. for 20 minutes. The precipitated lead sulfide was filtered off and the filtrate was neutralized to give 5 g of 6-ethoxy-3-pyridylcyanamide as colorless needles melting 102°-104° C.

Workup

  1. filtrationthe resulting crystals (m.p. 130°-133° C.) were recovered by filtration
  2. waitboiled with 50 ml of 10% sodium hydroxide for 15 minutes
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-80d5f6f353de4873883403eac8a462d2
Source dataset
uspto-grants-1982_07
Patent number
US04341769

Reaction notes

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