Acetone → 4,4'-Diamino-6-cyanobenzanilide

HRID 2323

Reaction equation

HRID 2323 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[NH2:10][C:11]1[CH:26]=[C:25]([C:27](=O)[NH2:28])[C:14]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)=[O:16])=[CH:13][CH:12]=1.[NH4+].[OH-].CC(C)=O>C(O)C>[NH2:10][C:11]1[CH:26]=[C:25]([C:27]#[N:28])[C:14]([C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[O:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14923Ammonium HydroxideHCID 24681Fuming sulfuric acidHCID 196897514,4'-Diamino-6-carbamoyl benzanilide

Product 1

HCID 196897504,4'-Diamino-6-cyanobenzanilide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

350 ml of oleum (30% by weight) was cooled down below 0° C. using an ice bath, 99.6 g (0.368 mol) of 4,4'-diamino-6-carbamoyl benzanilide in a powder form was added below 5° C. with stirring. The stirring was continued to the next day, and the solution was neutralized by adding 1100 ml of NH4OH (28% by weight) already cooled down to -5° to 0° C. The solution was sufficiently washed to remove salt by filtering and washed with a small amount of warm ethanol and then dried in a vacuum oven at 80° C. The dried reactant which was mixed with by-products was extracted by soxlet and treated with the activated carbon and then ethanol was added to recrystallize in the mixture solvent (acetone:ethanol=1:1). The light yellow-scalelike crystal was filtered and dried in a vacuum oven at 80° C. The light yellow-scalelike crystal was extracted again by soxlet with acetone and treated with the activated carbon. And then the white-scalelike crystal obtained by recrystalling in the mixture solvent (acetone:ethanol=1:1) was dried in a vacuum oven at 80° C. (40 g of the raw material was obtained and the boiling point thereof was 250° to 251° C.).

Workup

  1. temperaturealready cooled down to -5° to 0° C
  2. washThe solution was sufficiently washed
  3. customto remove salt
  4. filtrationby filtering
  5. washwashed with a small amount of warm ethanol
  6. customdried in a vacuum oven at 80° C
  7. additionThe dried reactant which was mixed with by-products
  8. extractionwas extracted by soxlet
  9. additiontreated with the activated carbon
  10. additionethanol was added
  11. customto recrystallize in the mixture solvent (acetone:ethanol=1:1)
  12. filtrationThe light yellow-scalelike crystal was filtered
  13. customdried in a vacuum oven at 80° C
  14. extractionThe light yellow-scalelike crystal was extracted again by soxlet with acetone
  15. additiontreated with the activated carbon
  16. customAnd then the white-scalelike crystal obtained
  17. dry with materialwas dried in a vacuum oven at 80° C. (40 g of the raw material
  18. customwas obtained
  19. customthereof was 250° to 251° C.

Sources & evidence

ORD record
ord-202ad24f23144e29a486e05cf3ccb4db
Source dataset
uspto-grants-1998_03
Patent number
US05728799

Linked notes

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