2,3-Dichlorobenzaldehyde → HCID 19980858, compound

HRID 1461477Notes

Reaction equation

HRID 1461477 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](/[CH3:45])=[CH:30]\[C:31]([O:33][CH2:34][CH2:35][N:36]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:37])=[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]([CH3:45])=[C:30]([C:31]([O:33][CH2:34][CH2:35][N:36]([CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH3:37])=[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 125291882-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoateHCID 19980844tert-Butyl 6-oxo-1,4-thiazepane-4-carboxylate 1,1-dioxide

Product 1

HCID 19980858HCID 19980858, compoundYield 50.3%

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-thiazepin-6-one (8.39 g, 31.9 mmole) from Example 6, 2,3-dichlorobenzaldehyde (5.58 g, 31.9 mmole) and 2-(N-benzyl-N-methylamino)ethyl 3-aminocrotonate (7.91 31.9 mmole) were heated to reflux in 40 mL of ethanol for 17 hours. The reaction was cooled to room temperature, filtered, and the solid washed with 50 mL of ether to obtain the title compound (10.72 g, 50% yield) D.C.I.M.S. (M+H) 668.

Workup

  1. temperaturewere heated
  2. filtrationfiltered
  3. washthe solid washed with 50 mL of ether

Sources & evidence

ORD record
ord-816ded081e6e484c8454bdc2c8480857
Source dataset
uspto-grants-1991_12
Patent number
US05075440

Reaction notes

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