Terephthaloyl chloride → HCID 269824, compound

HRID 2058100Notes

Reaction equation

HRID 2058100 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([Cl:11])[CH:5]=1)([O-:3])=[O:2].[C:12](Cl)(=[O:22])[C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>CN(C)P(N(C)C)(N(C)C)=O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:12](=[O:22])[C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:8][C:7]3[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[Cl:11])=[O:18])=[CH:15][CH:14]=2)=[C:6]([Cl:11])[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7488Terephthaloyl chlorideHCID 84922-Chloro-4-nitroaniline

Product 1

HCID 269824HCID 269824, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

In a 1 l. three-neck round bottom flask provided with a stirrer, nitrogen inlet and drying tube, a solution of 52.56 g. (0.3 mole) 4-nitro-2-chloroaniline (recrystallized from water) in 250 ml. of distilled hexamethylphosphoramide is prepared. The solution is cooled with an ice bath, and 30.45 g. (0.15 mole) terephthaloyl chloride is added in small portions over a period of 11/2 hours. After the addition is completed, the ice-bath is removed. A precipitate forms in four hours and the resulting suspension is stirred for 20 hours. After this period 1 l, of water is added to precipitate the product. The pale yellow powder is filtered, and washed two times with hot water in a blender. After being dried at 80° C. in a vacuum oven, 68.2 g. (95 percent of theoretical) of product is obtained; m.p. 339° C. (determined by Differential Thermal Analysis).

Workup

  1. customthree-neck round bottom flask provided with a stirrer, nitrogen inlet
  2. customdrying tube
  3. temperatureThe solution is cooled with an ice bath
  4. additionAfter the addition
  5. customthe ice-bath is removed
  6. waitAfter this period 1 l
  7. additionof water is added
  8. customto precipitate the product
  9. filtrationThe pale yellow powder is filtered
  10. washwashed two times with hot water in a blender
  11. customAfter being dried at 80° C. in a vacuum oven, 68.2 g
  12. custom(95 percent of theoretical) of product is obtained

Sources & evidence

ORD record
ord-6b99e53d849c429fb83d55538d172f1e
Source dataset
uspto-grants-1980_07
Patent number
USRE030352

Reaction notes

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