Chloroacetaldehyde → N-(4-Fluorophenyl)thiazol-2-amine

HRID 507621Notes

Reaction equation

HRID 507621 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][CH:3]=1.Cl[CH2:13][CH:14]=O.C(OCC)(=O)C>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:13]=[CH:14][N:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 8857Ethyl AcetateHCID 6930614-Fluorophenylthiourea

Product 1

HCID 25093329N-(4-Fluorophenyl)thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-fluorophenyl)thiourea (2.00 g, 11.7 mmol) and 2-chloroacetaldehyde(3.72 mL, 58.6 mmol) in anhydrous ethanol (5 mL) were added to a microwave vial. The reaction mixture was heated to 80° C. in a microwave reactor for 20 min. On cooling, ethyl acetate (2 mL) was added to the crude product reaction mixture and pure product crystallized out. This filtered off, washed with hexane and air-dried to afford the title compound as a crystalline brown solid, 1.568 g. MS (M+H)+ 195.

Workup

  1. temperatureOn cooling
  2. customcrystallized out
  3. filtrationThis filtered off
  4. washwashed with hexane
  5. customair-dried

Sources & evidence

ORD record
ord-1acfa439f8f64620a019ec581830f11f
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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