Sodium Acetate → 4-(4-Methoxy-phenyl)-5-phenylethyl-thiazol-2-ylamine

HRID 556094Notes

Reaction equation

HRID 556094 reaction equation
Br[CH:2]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[NH2:21][C:22]([NH2:24])=[S:23].C([O-])(=O)C.[Na+]>>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:21]=[C:22]([NH2:24])[S:23][C:2]=2[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 866366332-Bromo-1-(4-methoxy-phenyl)-4-phenyl-butan-1-one

Product 1

HCID 579916324-(4-Methoxy-phenyl)-5-phenylethyl-thiazol-2-ylamineYield 85.9%

Procedure

A procedure similar to step 5 of Example 6 was used. 2-bromo-1-(4-methoxy-phenyl)-4-phenyl-butan-1-one prepared in the step 3, thiourea and anhydrous sodium acetate were used as starting materials, refluxed for 3 hours, followed by post-treatment to give a crude product, which was recrystallized with anhydrous ethanol to obtain a product as a white solid in a yield of 85.9%, mp: 143-144 └. 1H-NMR (CDCl3, 400 MHz) δ: 2.90 (2H, t, J=7.60 Hz, CH2), 3.05 (2H, t, J=7.60 Hz, CH2), 3.82 (3H, s, OCH3), 4.99 (2H, br, NH2), 6.89 (2H, d, J=8.40 Hz, ArH), 7.12˜7.30 (5H, m, ArH), 7.35 (2H, d, J=8.40 Hz, ArH); EI-MS m/e (%): 310.1 (M+, 23), 219.1 (100), 177.1 (39); HREI-MS Calcd. for C18H18N2OS: 310.1140. found: 310.1140. Anal. Calcd. for C18H18N2OS: C, 69.65; H, 5.84; N, 9.02. found: C, 69.74; H, 5.86; N, 9.03.

Workup

  1. temperaturerefluxed for 3 hours
  2. customto give a crude product, which
  3. customwas recrystallized with anhydrous ethanol

Sources & evidence

ORD record
ord-cc165ea8a2d44a6b8293123abdb57e93
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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