Sodium Acetate → 4-(4-Fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

HRID 556042Notes

Reaction equation

HRID 556042 reaction equation
Br[CH:2]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[NH2:22][C:23]([NH2:25])=[S:24].C([O-])(=O)C.[Na+]>>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:22]=[C:23]([NH2:25])[S:24][C:2]=2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 866366262-Bromo-1-(4-fluoro-phenyl)-3-(4-nitro-phenyl)-propan-1-one

Product 1

HCID 579916194-(4-Fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamineYield 71.4%

Procedure

A procedure similar to step 5 of Example 6 was used. 2-bromo-1-(4-fluoro-phenyl)-3-(4-nitro-phenyl)-propan-1-one prepared in the step 2, thiourea and anhydrous sodium acetate were used as starting materials. The obtained crude product was recrystallized with a solvent mixture of ethyl acetate and acetone to give a product, which was a yellow solid in a yield of 71.4%, mp: 217-218 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.22 (2H, s, CH2), 6.99 (2H, s, NH2), 7.21 (2H, t, 3JFH=3JHH=8.72 Hz, ArH), 7.47 (2H, d, J=8.96 Hz, ArH), 8.03 (2H, dd, 3JHH=9.02, 4JFH=5.60 Hz, ArH), 8.19 (2H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 329.1 (M+, 100), 207.0 (21); HREI-MS Calcd. for C16H12FN3O2S: 329.0634. found: 329.0627. Anal. Calcd. for C16H12FN3O2S: C, 58.35; H, 3.67; N, 12.76. found: C, 58.61; H, 3.52; N, 12.61.

Workup

  1. customThe obtained crude product
  2. customwas recrystallized with a solvent mixture of ethyl acetate and acetone
  3. customto give a product, which

Sources & evidence

ORD record
ord-d67aa4ada95e46af985574f4d3e521d0
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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