Ethanol → 3-Oxo-N-(2-oxo-2H-benzo[d]imidazol-5-yl)butanamide

HRID 2260342Notes

Reaction equation

HRID 2260342 reaction equation
C(O)C.[NH2:4][C:5]1[CH:14]=[CH:13][C:8]2=[N:9][C:10](=[O:12])[N:11]=[C:7]2[CH:6]=1.[CH2:15]=[C:16]1[O:20][C:18](=[O:19])[CH2:17]1>O>[C:18]([NH:4][C:5]1[CH:14]=[CH:13][C:8]2=[N:9][C:10](=[O:12])[N:11]=[C:7]2[CH:6]=1)(=[O:19])[CH2:17][C:16]([CH3:15])=[O:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 12661DiketeneHCID 152505475-amino-2H-1,3-benzodiazol-2-one

Product 1

HCID 117760583-Oxo-N-(2-oxo-2H-benzo[d]imidazol-5-yl)butanamideYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mother liquor obtained is re-used in four further reaction cycles by using it at 80° C. to replace fresh ethanol containing 50% by weight of water for dissolving 2.86 kg per hour of 5-amino-2-benzimidazolone at such a rate that 26.86 kg per hour of amine solution can be reacted as described above with 2.06 kg per hour of diketene. Workup gives 4.25 to 4.34 kg per hour of 5-acetoacetylamino-2-benzimidazolone of consistent quality, corresponding to a yield of 95 to 97% based on amine.

Workup

  1. customThe mother liquor obtained
  2. customis re-used in four further reaction cycles
  3. customat 80° C.
  4. customcan be reacted

Sources & evidence

ORD record
ord-ba4e97b740534a449ee4b535c8992385
Source dataset
uspto-grants-1995_12
Patent number
US05476948

Reaction notes

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