4-Azidophenacyl bromide → 4-(4-Azidophenyl)thiazol-2-amine

HRID 2190314Notes

Reaction equation

HRID 2190314 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11]Br)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[NH2:14][C:15]([NH2:17])=[S:16].C([O-])(O)=O.[Na+]>CCO.O>[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:15]([NH2:17])[S:16][CH:11]=2)=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 926274-Azidophenacyl bromideHCID 516892Sodium BicarbonateHCID 2723790Thiourea

Product 1

HCID 123647384-(4-Azidophenyl)thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-(4-azidophenyl)-2-bromoethanone (1.37 g, 5.71 mmol) in EtOH (15 mL) at room temperature was added thiourea (0.476 g, 6.25 mmol). The reaction mixture was heated to 70° C. for 3 d, poured into a solution of NaHCO3 (602 mg) in water (50 mL) and stirred for 30 min. The precipitate that formed was collected by filtration, washed with water, and dried under high vacuum to give 4-(4-azidophenyl)thiazol-2-amine.

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-84b7596d78144ce4b769948b1bd95ecc
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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