Water → HCID 44477421, compound

HRID 1500117Notes

Reaction equation

HRID 1500117 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]#[N:18])=[C:15]([SH:19])[N:14]=[C:13]([O:20][CH3:21])[C:12]=2[C:22]#[N:23])=[CH:7][CH:6]=1.Cl[CH2:25][C:26]1[N:27]=[C:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[S:29][CH:30]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C.CO>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([C:28]2[S:29][CH:30]=[C:26]([CH2:25][S:19][C:15]3[C:16]([C:17]#[N:18])=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=4)[C:12]([C:22]#[N:23])=[C:13]([O:20][CH3:21])[N:14]=3)[N:27]=2)=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178494293HCID 178494293, compound

Product 1

HCID 44477421HCID 44477421, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

2.095 g (6.399 mmol) of 4-[4-(2-hydroxyethoxy)phenyl]-2-methoxy-6-sulphanylpyridine-3,5-dicarbonitrile together with 1.875 g (7.679 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 1.613 g (19.197 mmol) of sodium bicarbonate in 50 ml of DMF are stirred at room temperature overnight. Water and methanol are added, and the reaction mixture is placed in an ultrasonic bath for 2 minutes. A white solid precipitates out and is filtered off, washed with methanol and dried under high vacuum. The mother liquor is concentrated to half of the original volume and placed in the fridge for 30 minutes. The precipitated solid is filtered off, washed with methanol and dried under high vacuum. The two precipitated solids are combined, giving a total of 2.98 g (85% of theory) of the target compound.

Workup

  1. customA white solid precipitates out and
  2. filtrationis filtered off
  3. washwashed with methanol
  4. customdried under high vacuum
  5. concentrationThe mother liquor is concentrated to half of the original volume
  6. waitplaced in the fridge for 30 minutes
  7. filtrationThe precipitated solid is filtered off
  8. washwashed with methanol
  9. customdried under high vacuum
  10. customgiving a total of 2.98 g (85% of theory) of the target compound

Sources & evidence

ORD record
ord-8f660bf4e40b41e7bf0f6186b22cc586
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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