Methylamine → HCID 178485323, compound

HRID 1650170Notes

Reaction equation

HRID 1650170 reaction equation
Cl.[OH:2][C:3]1[C:12]([CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([NH:7][CH3:8])=[O:6].OC1C(CC2N=CNC=2)=CC=CC=1C(OC)=O.CN>C(O)C>[OH:2][C:3]1[C:12]([CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([NH:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 178485324HCID 178485324, compoundHCID 178497710HCID 178497710, compound

Product 1

HCID 178485323HCID 178485323, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-N-methylbenzamide hydrochloride. 6.96 g (30 mmoles) of methyl 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate (prepared in Example 1.B.2.) and 60 ml of methylamine dissolved in 350 ml of ethanol, are heated in an autoclave at 75° C. for 3 hours. The mixture is evaporated under reduced pressure. The residue is taken up in water and extracted three times with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica gel (eluent: 91.5:8.0:0.5 v/v/v dichloromethane-methanol-ammonia). After the solvents have been evaporated, the product thus obtained is crystallized from ethyl acetate. 4.95 g of 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-N-methlbenzamide is obtained. Yield: 71%.

Workup

  1. customThe mixture is evaporated under reduced pressure
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is purified by chromatography on silica gel (eluent: 91.5:8.0:0.5 v/v/v dichloromethane-methanol-ammonia)
  6. customAfter the solvents have been evaporated
  7. customthe product thus obtained
  8. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-676ed8175a214f2ba52ab3ad4a88413f
Source dataset
uspto-grants-1990_05
Patent number
US04923865

Reaction notes

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