Ammonium Chloride → HCID 178491911, compound

HRID 2112245Notes

Reaction equation

HRID 2112245 reaction equation
[Cl:1][C:2]1([O:22][CH3:23])[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([C:10]([CH2:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])=[O:11])[NH:3]1.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:1][C:2]1([O:22][CH3:23])[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH:10]([OH:11])[CH2:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[NH:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 178491910HCID 178491910, compound

Product 1

HCID 178491911HCID 178491911, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a reactor were placed 1.00 g (3.0 m moles) of 4-chloro-2-(4,6-dimethoxypyrimidine-2-ylcarbonyl)acetanilide and 20 ml of ethanol. The reactor contents were cooled to 5° C. or less. Thereto was added 0.25 g (6.6 m moles) of sodium borohydride. The mixture was stirred at the same temperature for 1 hour. Then, the temperature was increased to room temperature. After the completion of the reaction, an aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic layer was concentrated. The concentrate was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 0.69 g (2.0 m moles) of 4-chloro-2-(4,6-dimethoxypyrimidine-2-ylhydroxymethyl)acetanilide. Yield: 68%

Workup

  1. customIn a reactor were placed
  2. temperatureThe reactor contents were cooled to 5° C. or less
  3. customAfter the completion of the reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customThe concentrate was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-3bfcc842a75d4ef3a15cdae5e9a4735d
Source dataset
uspto-grants-2009_04
Patent number
US07521555B2

Reaction notes

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