Sodium Hydroxide → HCID 18790614, compound

HRID 1107005Notes

Reaction equation

HRID 1107005 reaction equation
Br.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16]C(=O)C(F)(F)F)=[CH:10][CH:9]=2)[N:7]=1.[OH-].[Na+]>CO.O>[NH2:16][CH2:15][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[N:7]=[C:3]([NH2:2])[S:4][CH:5]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18790616HCID 18790616, compound

Product 1

HCID 18790614HCID 18790614, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

4-{4-(2-Aminoethyl)phenyl}-2-thiazolamine: A solution of N-{2-{4-(2-bromoacetyl)phenyl}ethyl}-2,2,2-trifluoroacetamide (5.55 g, 16.4 mmol), prepared in Example 1(b), and thiourea (1.25 g, 16.4 mmol) in isopropanol (60 mL) was heated at reflux for 1 h. The reaction mixture was concentrated under reduced pressure to give crude N-{2-{4-(2-amino-4-thiazolyl)phenyl}ethyl}-2,2,2-trifluoroacetamide hydrobromide (6.51 g, ~100% yield). A solution of the crude hydrobromide and aqueous 4N NaOH (14.3 mL, 57.4 mmol) in MeOH (70 mL) and H2O (10 mL) was heated at reflux for 20 min. The solution was cooled, H2O (30 mL) was added and the MeOH was carefully evaporated under reduced pressure while keeping the solution cool. The resulting suspension was cooled to 0°. The crystals obtained by filtration were washed with cold H2O then air-dried to give 4-{4-(2-aminoethyl)phenyl}-2-thiazolamine (3.3 g, 92% yield): 1H NMR (DMSO-d6) δ 7.69 (d, J=8.2 Hz, 2H), 7.18 (d, J=8.2 Hz, 2H), 7.03 (broad s, 2H), 6.92 (s, 1H), 2.76 (t, J=7.1 Hz, 2H), 2.62 (t, J=7.1 Hz, 2H).

Workup

  1. temperatureat reflux for 20 min
  2. temperatureThe solution was cooled
  3. customthe MeOH was carefully evaporated under reduced pressure
  4. temperaturecool
  5. temperatureThe resulting suspension was cooled to 0°
  6. customThe crystals obtained by filtration
  7. washwere washed with cold H2O
  8. customthen air-dried

Sources & evidence

ORD record
ord-a53c3ff11f0d46cfac473e2573083c12
Source dataset
uspto-grants-2000_05
Patent number
US06057451

Reaction notes

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