Formamide → 2-[4-[4-(Pyrimidin-4-yl)phenoxy]butyl]-1H-isoindole-1,3(2H)-dione

HRID 1417318Notes

Reaction equation

HRID 1417318 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:6][CH:5]=1)(=O)[CH3:2].[CH:26]([NH:28][CH:29](NC=O)[NH:30]C=O)=O.C(N)=O.[OH-].[Na+]>O>[N:28]1[CH:26]=[CH:2][C:1]([C:4]2[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]3=[O:23])=[CH:6][CH:5]=2)=[N:30][CH:29]=1

Participants

6

Reactant 4

HCID 713FormamideHCID 14798Sodium HydroxideHCID 78505N,N',N''-MethylidynetrisformamideHCID 675980872-[4-(4-Acetylphenoxy)butyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 675995062-[4-[4-(Pyrimidin-4-yl)phenoxy]butyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.0 g of 2-[4-(4-acetylphenoxy]-butyl]-1H-isoindole-1,3(2H)-dione (Example 42) 10.0 g of tris(formamido)methane, and 20 ml of formamide are combined and the mixture stirred and heated at 160°-165° C. for 8 hours. After dilution with 100 ml of water, the mixture is rendered basic with 10N NaOH, the precipitate collected, washed with water, and air dried. Recrystallization from ethanol gives the pure compound, m.p. 100°-102° C.; yield, 5.0 g.

Workup

  1. temperatureheated at 160°-165° C. for 8 hours
  2. customthe precipitate collected
  3. washwashed with water, and air
  4. customdried
  5. customRecrystallization from ethanol
  6. customgives the pure compound, m.p. 100°-102° C.
  7. customyield

Sources & evidence

ORD record
ord-14a0374f1cf0424bb6cd26c83a98c3ef
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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