Sodium Acetate → 4-(2-Amino-4-thiazolyl)-2-methoxy-6-nitrophenol

HRID 274463

Reaction equation

HRID 274463 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([O:15][CH3:16])[CH:6]=1)=O.[NH2:17][C:18]([NH2:20])=[S:19].C([O-])(=O)C.[Na+]>C(O)C>[NH2:20][C:18]1[S:19][CH:2]=[C:3]([C:5]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([O:15][CH3:16])[CH:6]=2)[N:17]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 144509832-Bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone

Product 1

HCID 214592034-(2-Amino-4-thiazolyl)-2-methoxy-6-nitrophenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

aaa) A suspension of 2.9 g of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone and 761.2 mg of thiourea in 170 ml of ethanol is treated at 60° with 820.3 mg of sodium acetate and stirred for 6 hours. The reaction mixture is then evaporated, the residue is treated with 170 ml of water and heated to 60° for 30 minutes. After cooling the product is filtered under suction and washed with water. There is obtained 4-(2-amino-4-thiazolyl)-2-methoxy-6-nitrophenol of m.p. 248°-250° (from ethanol).

Workup

  1. customThe reaction mixture is then evaporated
  2. additionthe residue is treated with 170 ml of water
  3. temperatureheated to 60° for 30 minutes
  4. temperatureAfter cooling the product
  5. filtrationis filtered under suction
  6. washwashed with water

Sources & evidence

ORD record
ord-c3e529e313334920b3472eced7f1ee5b
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Linked notes

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