Ammonia → HCID 23362222, compound

HRID 1082110Notes

Reaction equation

HRID 1082110 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([Cl:27])[C:23](OC)=[O:24])=[CH:17][CH:16]=1)[CH3:11].O1CCCC1.[NH3:33]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([Cl:27])[C:23]([NH2:33])=[O:24])=[CH:17][CH:16]=1)[CH3:11]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 15186152HCID 15186152, compound

Product 1

HCID 23362222HCID 23362222, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-chloropropanoate (2.36 g), tetrahydrofuran (40 mL), methanol (40 mL) and aqueous ammonia solution (specific gravity 0.88; 40 mL) was stirred at room temperature for 2.5 hrs. The organic solvents were evaporated in vacuo and the residue was diluted with water (1 L) and extracted with dichloromethane (3×400 mL). The combined dichloromethane layers were washed with dilute hydrochloric acid solution (2M; 400 mL), water (1 L), brine (1 L), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 1.5% methanol in dichloromethane as eluent to afford the title compound, mp 149°-151° C. after recrystallisation from dichloromethane-hexane.

Workup

  1. customThe organic solvents were evaporated in vacuo
  2. additionthe residue was diluted with water (1 L)
  3. extractionextracted with dichloromethane (3×400 mL)
  4. washThe combined dichloromethane layers were washed with dilute hydrochloric acid solution (2M; 400 mL), water (1 L), brine (1 L)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel with 1.5% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-7cbdc07b2cc1409a865f277877679222
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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