Acetic Acid → HCID 53777669, compound

HRID 362288Notes

Reaction equation

HRID 362288 reaction equation
[NH2:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][N:17]([C:19]2[O:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)[CH3:18])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C(O)(=O)C.[N:32](OCCC(C)C)=O>C(Cl)(Cl)Cl>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[N:17]([CH2:16][CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C:2](=[N+:1]=[N-:32])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1)[CH3:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8053Isoamyl NitriteHCID 10499318HCID 10499318, compound

Product 1

HCID 53777669HCID 53777669, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of methyl 2-amino-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]propanoate (5.00 g), acetic acid (4.4 mL) and chloroform (160 mL) was treated dropwise with isoamyl nitrite (3.2 mL). The mixture was heated at reflux for 1.5 hrs, cooled, diluted with chloroform (200 mL) and washed successively with dilute hydrochloric acid (200 mL), water (2×200 mL) and brine (200 mL). The chloroform solution was dried over MgSO4, evaporated and the residue chromatographed on silica gel using 3% ethyl acetate in dichloromethane as eluent to afford the title compound, a gum.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1.5 hrs
  3. temperaturecooled
  4. washwashed successively with dilute hydrochloric acid (200 mL), water (2×200 mL) and brine (200 mL)
  5. dry with materialThe chloroform solution was dried over MgSO4
  6. customevaporated
  7. customthe residue chromatographed on silica gel using 3% ethyl acetate in dichloromethane as eluent

Sources & evidence

ORD record
ord-1a13adeba1ae4dbd8da0696ed0afc663
Source dataset
uspto-grants-1999_02
Patent number
US05869495

Reaction notes

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