Thiourea → 3-(2-Amino-thiazol-4-yl)-benzonitrile

HRID 619073Notes

Reaction equation

HRID 619073 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])=O.[NH2:13][C:14]([NH2:16])=[S:15]>CO>[NH2:16][C:14]1[S:15][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[C:8]#[N:9])[N:13]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 27358673-(2-Bromoacetyl)benzonitrile

Product 1

HCID 27565583-(2-Amino-thiazol-4-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

16.9 g of 3-bromoacetyl-benzonitrile were placed in 50 ml of methanol and treated at room temperature with 8 g of thiourea. The mixture was boiled for 21/2 hours and then cooled to 0° C. while stirring slowly. The product separated as the salt, was filtered off and converted into the base by the addition of 100 ml of 2N sodium hydroxide solution. The aqueous suspension was extracted with a total of 700 ml of methylene chloride and the organic phase was dried with magnesium sulphate. 9.6 g of 3-(2-amino-thiazol-4-yl)-benzonitrile separated upon concentration.

Workup

  1. custom2 hours
  2. customThe product separated as the salt
  3. filtrationwas filtered off
  4. additionconverted into the base by the addition of 100 ml of 2N sodium hydroxide solution
  5. extractionThe aqueous suspension was extracted with a total of 700 ml of methylene chloride
  6. dry with materialthe organic phase was dried with magnesium sulphate
  7. custom9.6 g of 3-(2-amino-thiazol-4-yl)-benzonitrile separated upon concentration

Sources & evidence

ORD record
ord-c619c38e7f764e81ae870da8f49dac2f
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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