Sodium Acetate → HCID 57991594, compound

HRID 556100Notes

Reaction equation

HRID 556100 reaction equation
Br[CH:2]([CH2:13][CH2:14][CH2:15][CH3:16])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[NH2:17][C:18]([NH2:20])=[S:19].C([O-])(=O)C.[Na+]>>[CH2:13]([C:2]1[S:19][C:18]([NH2:20])=[N:17][C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 109349931-Hexanone, 2-bromo-1-(4-methoxyphenyl)-

Product 1

HCID 57991594HCID 57991594, compoundYield 57.2%

Procedure

A procedure similar to step 5 of Example 6 was used. 2-bromo-1-(4-methoxy-phenyl)-hexan-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 petroleum ether and ethyl acetate at a ratio of 1:1 (V:V) to obtain a product as a white solid in a yield of 57.2%, mp: 118-119 └. 1H-NMR (CDCl3, 400 M.Hz) δ: 0.90 (3H, t, J=7.2 Hz, CH3), 1.36 (2H, sextuple, J=7.20 Hz, CH2), 1.59 (2H, quintuple, J=7.20 Hz, CH2), 2.74 (2H, t, J=7.2 Hz, CH3), 3.83 (3H, s, OCH3), 4.93 (2H, br, NH2), 6.93 (2H, d, J=8.80 Hz, ArH), 7.45 (2H, d, J=8.80 Hz, ArH); EI-MS m/e (%): 262.0 (M+, 55), 219.0 (100), 177.0 (36); HREI-MS Calcd. for C14H18N2OS: 262.1140. found: 262.1140. Anal. Calcd. for C14H18N2OS: C, 64.09; H, 6.92; N, 10.68. found: C, 64.19; H, 7.02; N, 10.63.

Workup

  1. temperaturerefluxed for 3 hours
  2. customto give a crude product, which
  3. customwas recrystallized with petroleum ether and ethyl acetate at a ratio of 1:1 (V:V)

Sources & evidence

ORD record
ord-1ed45da7e6df4833b15d83fe7a036cc5
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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