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

HRID 1112728Notes

Reaction equation

HRID 1112728 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 1 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 1 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-f10efe7a9aa44591abc875be517b8dd0
Source dataset
uspto-grants-1978_10
Patent number
US04123541

Reaction notes

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