Hydrochloric Acid → HCID 22152540, compound

HRID 232393Notes

Reaction equation

HRID 232393 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:21])[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)=[CH:6][CH:5]=1.[OH-].[K+].Cl>CC(N(C)C)=O.CO>[N+:18]([C:14]1[CH:13]=[C:12]([NH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:22])=[O:2])=[CH:5][CH:6]=2)=[O:21])[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4363454HCID 4363454, compound

Product 1

HCID 22152540HCID 22152540, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

Into a 10 l flask fitted with an inlet tube for nitrogen, a mechanical stirrer, a dropping funnel, and a thermometer were introduced at room temperature 500 g (1.66 moles) of methyl-4-(m-nitrophenylcarbamoyl)benzoate in 4 l of dimethylacetamide. To the yellow solution there was added dropwise with stirring and cooling a solution of 231 g (85%) of KOH (3.5 moles) in 1 l of methanol. Subsequently, the orange solution was stirred for another hour at 60° C. Next, the reaction mixture was acidified with a dilute solution of hydrochloric acid. The resulting precipitate was filtered, washed with water, and dried in vacuo. Obtained were 457 g of the envisaged product with a melting point of 319° C. (DSC) in a yield of 96%.

Workup

  1. customInto a 10 l flask fitted with an inlet tube for nitrogen, a mechanical stirrer, a dropping funnel
  2. additionTo the yellow solution there was added dropwise
  3. stirringSubsequently, the orange solution was stirred for another hour at 60° C
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo
  7. customObtained

Sources & evidence

ORD record
ord-c2aa7b93a2e64e12b189987764b2f73e
Source dataset
uspto-grants-1989_07
Patent number
US04851562

Reaction notes

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