2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → HCID 178424322, compound

HRID 1879503Notes

Reaction equation

HRID 1879503 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[CH2:11][S:10]/[C:9]/1=[N:14]\[CH:15]([CH3:17])[CH3:16].[O:18]1[C:23]2[CH:24]=[CH:25][C:26]([CH:28]=O)=[CH:27][C:22]=2[O:21][CH2:20][CH2:19]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[O:18]1[C:23]2[CH:24]=[CH:25][C:26](/[CH:28]=[C:11]3/[C:12](=[O:13])[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])/[C:9](=[N:14]/[CH:15]([CH3:17])[CH3:16])/[S:10]/3)=[CH:27][C:22]=2[O:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 517045Sodium AcetateHCID 178424323HCID 178424323, compound

Product 1

HCID 178424322HCID 178424322, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(2-methyl phenyl)-2-[(Z)-isopropylimino]-thiazolidin-4-one (50 mg, 0.200 mmol), 2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde (49 mg, 0.300 mmol) and sodium acetate (33 mg, 0.400 mmol) in acetic acid (1 mL) is stirred at 110° C. for 5 h. The reaction mixture is cooled to rt and subjected to prep. HPLC purification. The product containing fractions are evaporated and dried to give 5-(2,3-dihydro-benzo[1,4]dioxin-6-ylmeth-(Z)-yl idene)-2-[(Z)-isopropylimino]-3-o-tolyl-thiazolidin-4-one.

Workup

  1. customHPLC purification
  2. additionThe product containing fractions
  3. customare evaporated
  4. customdried

Sources & evidence

ORD record
ord-3ef4d429b2cd413dad954d92a4254db1
Source dataset
uspto-grants-2012_11
Patent number
USRE043833E1

Reaction notes

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