Hydrazine hydrate (1:1) → 2-Oxazolemethanamine, 5-(4-chlorophenyl)-, monohydrochloride

HRID 866853Notes

Reaction equation

HRID 866853 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH2:13][N:14]3C(=O)C4=CC=CC=C4C3=O)=[N:10][CH:9]=2)=[CH:4][CH:3]=1.O.NN>C(O)C>[ClH:1].[NH2:14][CH2:13][C:11]1[O:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22762753HCID 22762753, compound

Product 1

HCID 30492642-Oxazolemethanamine, 5-(4-chlorophenyl)-, monohydrochlorideYield 154.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.4 g of N-[5-(4-chlorophenyl)-2-oxazolyl]methylphthalimide and 0.55 g of 100% hydrazine hydrate in 50 ml of ethanol was heated at reflux for one hour. At the end of this period, the formed precipitate was filtered off, and the filtrate was evaporated to dryness in vacuo. The residue was shaken with 2N HCl - chloroform and the 2N HCl - layer was evaporated to dryness under vacuo. The residue was recrystallized from ethanol to give 1.9 g (78 percent) of 2-aminomethyl-5-(4-chlorophenyl) oxazole hydrochloride, M.P. 200° C (decomposition).

Workup

  1. temperatureat reflux for one hour
  2. filtrationAt the end of this period, the formed precipitate was filtered off
  3. customthe filtrate was evaporated to dryness in vacuo
  4. customthe 2N HCl - layer was evaporated to dryness under vacuo
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e9312d285a2d4482a7353beb8ea8e34e
Source dataset
uspto-grants-1978_07
Patent number
US04101660

Reaction notes

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