HCID 23353100, compound → HCID 136087735, compound

HRID 864282Notes

Reaction equation

HRID 864282 reaction equation
[C:1]([CH:5]1[C:10](=[O:11])[CH2:9][CH:8]([CH:12]2[CH2:17][CH2:16][CH2:15][S:14][CH2:13]2)[CH2:7][C:6]1=[O:18])(=O)[CH2:2][CH3:3].[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[CH:27][CH2:28][O:29][NH2:30])=[CH:22][CH:21]=1>CO>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]=[CH:27][CH2:28][O:29][N:30]=[C:1]([C:5]2[C:10](=[O:11])[CH2:9][CH:8]([CH:12]3[CH2:17][CH2:16][CH2:15][S:14][CH2:13]3)[CH2:7][C:6]=2[OH:18])[CH2:2][CH3:3])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 23353100HCID 23353100, compoundHCID 54468234HCID 54468234, compound

Product 1

HCID 136087735HCID 136087735, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.0 g (0.011 mol) of 2-propionyl-5-(3-tetrahydrothiopyranyl)-cyclohexane-1,3-dione and 3.0 g (0.013 mol) of 3-(4-bromophenyl)-prop-2-enyloxyamine in 100 ml of methanol were stirred for 16 hours at 20° C. The precipitated reaction product was filtered off under suction at 0° C. and washed with ice cold methanol and petroleum ether. Drying gave 3.7 g (68.4% of theory) of 2-[1-(3-(4-bromophenyl)-prop-2-enyloximino)-propyl]-3-hydroxy-5-(3-tetrahydrothiopyranyl)-cyclohex-2-en-1-one of melting point 97°-99° C.

Workup

  1. customThe precipitated reaction product
  2. filtrationwas filtered off under suction at 0° C.
  3. washwashed with ice cold methanol and petroleum ether
  4. customDrying

Sources & evidence

ORD record
ord-3c9e23eea6154a5eb4f7c691f23c19e8
Source dataset
uspto-grants-1996_10
Patent number
US05563114

Reaction notes

Loading…