Dimethylformamide → Diisopropyl Ether

HRID 2379880Notes

Reaction equation

HRID 2379880 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-06ea1b899b1341d6892aaf79d0b77bd9
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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