3,4-Dichlorobenzaldehyde → HCID 18187155, compound

HRID 1386046Notes

Reaction equation

HRID 1386046 reaction equation
[CH3:1][S:2]([CH2:5][C:6](=O)[CH3:7])(=[O:4])=[O:3].[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH:13]=O.[NH2:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH:21]=1>C(O)C>[Cl:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:21]3[C:22](=[O:26])[CH2:23][CH2:24][CH2:25][C:20]=3[NH:19][C:6]([CH3:7])=[C:5]2[S:2]([CH3:1])(=[O:4])=[O:3])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

5

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 786951-(Methylsulphonyl)acetoneHCID 788923-Aminocyclohex-2-en-1-one

Product 1

HCID 18187155HCID 18187155, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methanesulfonylacetone (135 mg, 1.00 mmol), 3,4-dichlorobenzaldehyde (175 mg, 1.00 mmol) and 3-amino-2-cyclohexen-1-one (111 mg, 1.00 mmol) in ethanol (7 mL) was heated to reflux for 24 hours and cooled. The solid that precipitated was collected, washed with ethanol, dried, and triturated with methanol to provide the title compound. MS (APCI) m/e 386 (M+H)+, 388 (M+H)+; 1H NMR (DMSO-d6) 1.75 (m, 1H), 1.90 (m, 1H), 2.21 (m, 2H), 2.32 (s, 3H), 2.50 (m, 2H), 2.73 (s, 3H), 4.94 (s, 1H), 7.18 (dd, 1H), 7.34 (d, 1H), 7.53 (d, 1H), 9.48 (br s, 1H), Anal. Calcd for C17H17Cl2NO3S: C, 52.86; H, 4.44; N, 3.63. Found: C, 52.91; H, 4.31; N, 3.55.

Workup

  1. temperatureto reflux for 24 hours
  2. temperaturecooled
  3. customThe solid that precipitated
  4. customwas collected
  5. washwashed with ethanol
  6. customdried
  7. customtriturated with methanol

Sources & evidence

ORD record
ord-1f1b4760146f43888b09cee8f5a9f5c7
Source dataset
uspto-grants-2001_07
Patent number
US06265417B1

Reaction notes

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