Acetic Acid → HCID 14933727, compound

HRID 1902498Notes

Reaction equation

HRID 1902498 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33].C(O)(=O)C>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:22][N:23]3[C:24](=[O:33])[C:25]4=[CH:32][CH:31]=[CH:30][CH:29]=[C:26]4[C:27]3=[O:28])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 150354-[(4-Nitrophenyl)azo]phenolHCID 24758Sodium hydrideHCID 87154Chloromethylphthalimide

Product 1

HCID 14933727HCID 14933727, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the red dye, 4-(4-nitro-phenylazo)phenol (0.5 g), in DMF was added sodium hydride (0.1 g of a 50% dispersion). After stirring for 5 minutes at room temperature, N-(chloromethyl)phthalimide (0.5 g) was added and stirring continued overnight. The solution was acidified with acetic acid and the product precipitated by pouring into ice water. The product recrystallized from ethyl acetate/cyclohexane, was obtained in 0.72 g yield, m.p. 182°-190° C.

Workup

  1. stirringstirring continued overnight
  2. customthe product precipitated
  3. additionby pouring into ice water
  4. customThe product recrystallized from ethyl acetate/cyclohexane
  5. customwas obtained in 0.72 g
  6. customyield

Sources & evidence

ORD record
ord-d513bdc0d0c14a8ab7da0a6940849435
Source dataset
uspto-grants-1982_12
Patent number
US04363865

Reaction notes

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