Dimethylformamide → Diisopropyl Ether

HRID 1491889Notes

Reaction equation

HRID 1491889 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Cl[CH2:14][C:15]1[CH:20]=[C:19]([C:21]2[N:22]=[C:23]([N:26]=[C:27]([NH2:29])[NH2:28])[S:24][CH:25]=2)[CH:18]=[CH:17][N:16]=1.CN(C)C=[O:33]>>[CH:15]([O:33][CH:9]([CH3:8])[CH3:10])([CH3:20])[CH3:14].[NH2:28][C:27](=[N:26][C:23]1[S:24][CH:25]=[C:21]([C:19]2[CH:18]=[CH:17][N:16]=[C:15]([CH2:14][N:5]3[C:1](=[O:11])[C:2]4=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]4[C:4]3=[O:6])[CH:20]=2)[N:22]=1)[NH2:29]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10333220HCID 10333220, compoundHCID 24194345Phthalimide potassium salt

Product 2

HCID 7914Diisopropyl EtherHCID 10474781HCID 10474781, compound

Procedure

Potassium phthalimide (1.65 g) was added to a solution of 4-(2-chloromethylpyridin-4-yl)-2-(diaminomethyleneamino)thiazole (2.39 g) in N,N-dimethylformamide (25 ml). After stirring for 14 hours, the solvent was evaporated in vacuo and the residue was mixed with water. The resulting precipitate was collected by filtration and washed with ethanol and then diisopropyl ether to give 2-(diaminomethyleneamino)-4-(2-phthalimidomethylpyridin-4-yl)thiazole (2.68 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionthe residue was mixed with water
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-90f331a2d78542cebd5e921e5d5f9a0c
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

Loading…