3,4,5-Trimethoxybenzaldehyde → 2-(3-oxo-4H-1,4-benzothiazin-2-yl)-N-[(E)-(3,4,5-trimethoxyphenyl)methylideneamino]acetamide

HRID 2059956Notes

Reaction equation

HRID 2059956 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][CH:3]1[CH2:12][C:13]([NH:15][NH2:16])=[O:14].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH:22]=O.ClCCCl.C(O)C>C(O)C.C(O)(=O)C>[O:1]=[C:2]1[CH:3]([CH2:12][C:13]([NH:15]/[N:16]=[CH:22]/[C:21]2[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:19]([O:18][CH3:17])[CH:20]=2)=[O:14])[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[NH:7]1

Participants

6

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 34500263,4-Dihydro-3-oxo-2H-1,4-benzothiazine-2-acetic acid hydrazideHCID 229016121,2-Dichloroethane ethanol

Product 1

HCID 249881172-(3-oxo-4H-1,4-benzothiazin-2-yl)-N-[(E)-(3,4,5-trimethoxyphenyl)methylideneamino]acetamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

In a round-bottom glass flask equipped with a magnetic stir bar (3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetic acid hydrazide (1 eq. 0.063 mmol; 15 mg) was dissolved in ethanol (3 mL) at room temperature. To this well stirred solution, acetic acid (˜3 drops) and 3,4,5-trimethoxy-benzaldehyde solution (0.063 mmol; 12.4 mg dissolved in 0.5 mL of ethanol) were added, and the reaction mixture was stirred for another 5 hours at ambient temperature and monitored by TLC (typically with 1,2-dichloroethane-ethanol 5:1). The mixture was then concentrated under vacuum using a rotary evaporator. The crude product was diluted with hexanes and triturated. The precipitated solid product was transferred to a glass fiber funnel, the supernatant was removed by vacuum filtration and the solid was washed thoroughly with n-hexane twice to yield: 16 mg (61%) of 1-1.

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. customa rotary evaporator
  3. additionThe crude product was diluted with hexanes
  4. customtriturated
  5. customThe precipitated solid product was transferred to a glass fiber funnel
  6. customthe supernatant was removed by vacuum filtration
  7. washthe solid was washed thoroughly with n-hexane twice to yield: 16 mg (61%) of 1-1

Sources & evidence

ORD record
ord-fa2ab42bcadf47c4a63fb6188a4d8419
Source dataset
uspto-grants-2012_10
Patent number
US08278327B2

Reaction notes

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