2,3-Dichlorobenzaldehyde → HCID 19980840, compound

HRID 1461480Notes

Reaction equation

HRID 1461480 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13](=[O:15])[CH2:12][S:11](=[O:17])(=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.[NH2:28]/[C:29](/[CH3:37])=[CH:30]\[C:31]([O:33][CH2:34][CH2:35][OH:36])=[O:32]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]2([OH:15])[NH:28][C:29]([CH3:37])=[C:30]([C:31]([O:33][CH2:34][CH2:35][OH:36])=[O:32])[CH:21]([C:20]3[CH:23]=[CH:24][CH:25]=[C:26]([Cl:27])[C:19]=3[Cl:18])[CH:12]2[S:11](=[O:16])(=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 19980844tert-Butyl 6-oxo-1,4-thiazepane-4-carboxylate 1,1-dioxideHCID 19980851HCID 19980851, compound

Product 1

HCID 19980840HCID 19980840, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-N-(t-butyloxycarbonyl)-1,1-dioxo -2,3,4,5,6,7-hexahydro-1,4-thiazepine-6-one (9.06 g, 34.5 mmole) from Example 6, 2,3-dichlorobenzaldehyde (6.03 g, 34.5 mmole) and 2-hydroxyethyl 3-aminocrotonate (5.00 g, 34.5 mmole) was heated to reflux in 200 mL of ethanol for 24 hours. The ethanol was removed under reduced pressure and the residue was heated in refluxing toluene for 2 hours. After cooling a precipitate was filtered to give 6.75 g of the title compound. Evaporation of the filtrate and chromatography (2.5:1, ethyl acetate:hexane) produced 3.78 g of product.

Workup

  1. temperaturewas heated
  2. customThe ethanol was removed under reduced pressure
  3. temperaturethe residue was heated
  4. temperaturein refluxing toluene for 2 hours
  5. temperatureAfter cooling a precipitate
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-466761ee21084fa98a049d377c505574
Source dataset
uspto-grants-1991_12
Patent number
US05075440

Reaction notes

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