Butylamine → N-[(4,5-Diphenyl-1,3-oxazol-2-yl)methyl]butan-1-amine--hydrogen chloride (1/1)

HRID 329209Notes

Reaction equation

HRID 329209 reaction equation
[Cl:1][CH2:2][C:3]1[O:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[CH2:20]([NH2:24])[CH2:21][CH2:22][CH3:23]>C1C=CC=CC=1>[ClH:1].[CH2:20]([NH:24][CH2:2][C:3]1[O:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 12413149HCID 12413149, compound

Product 1

HCID 214409N-[(4,5-Diphenyl-1,3-oxazol-2-yl)methyl]butan-1-amine--hydrogen chloride (1/1)Yield 72%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 8 g. 2-chloromethyl-4,5-diphenyl-oxazole (prepared as described in Example 1 a) and 6.6 g. n-butylamine in 100 ml. anhydrous benzene was refluxed for 4 hours. The reaction mixture was washed with water and the separated benzene phase was distilled at 20 mm. pressure. The oily residue was dissolved in 100 ml. anhydrous ether and a flow of gas hydrogen chloride was bubbled through the resulting solution. The 2-n-butylaminomethyl-4,5-diphenyloxazole hydrochloride was recrystallized from absolute ethanol/anhydrous diethyl ether: 7.4 g., m.p. 120°-123° C (yield 72%).

Workup

  1. washThe reaction mixture was washed with water
  2. distillationthe separated benzene phase was distilled at 20 mm
  3. dissolutionThe oily residue was dissolved in 100 ml
  4. customanhydrous ether and a flow of gas hydrogen chloride was bubbled through the resulting solution
  5. customThe 2-n-butylaminomethyl-4,5-diphenyloxazole hydrochloride was recrystallized from absolute ethanol/anhydrous diethyl ether

Sources & evidence

ORD record
ord-2648dacaf07f4168bb299a41cd54fe06
Source dataset
uspto-grants-1977_04
Patent number
US04020082

Reaction notes

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