2,3-Dichlorobenzaldehyde → HCID 19980855, compound

HRID 1461479Notes

Reaction equation

HRID 1461479 reaction equation
[O:1]=[S:2]1(=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH:13]=[O:14])[CH2:5][C:4](=O)[CH2:3]1.[Cl:17][C:18]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.[NH2:27]/[C:28](/[CH3:35])=[CH:29]\[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(O)C>[Cl:17][C:18]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]1[C:3]2[S:2](=[O:16])(=[O:1])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:6]([CH:13]=[O:14])[CH2:5][C:4]=2[NH:27][C:28]([CH3:35])=[C:29]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 19980861HCID 19980861, compound

Product 1

HCID 19980855HCID 19980855, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,1-dioxo-5-N-formyl-2,3,4,5-tetrahydro-[1,5]-benzothiazepin-3-one (0.410 g, 1.71 mmole) from Example 16, 2,3-dichlorobenzaldehyde (0.297 g, 1.71 mmole) and ethyl 3-aminocrotonate (0.219 g, 1.71 mmole) in 7 mL of ethanol was heated to reflux for 18 hours. The solvent was removed under reduced pressure and the residue was chromatographed (silica gel, 1:1 hexane:ethyl acetate) to obtain the product as an oil (0.75 g, 86% yield). The product was recrystallized from chloroform-ether.

Workup

  1. temperatureto reflux for 18 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was chromatographed (silica gel, 1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-39397a33f5a143e78accdfcf335d5115
Source dataset
uspto-grants-1991_12
Patent number
US05075440

Reaction notes

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