Methylamine → 1-(4,5-Diphenyl-1,3-oxazol-2-yl)-N-methylmethanamine--hydrogen chloride (1/1)

HRID 329207Notes

Reaction equation

HRID 329207 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.[CH3:20][NH2:21]>C1C=CC=CC=1>[ClH:1].[CH3:20][NH:21][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

Participants

4

Reactant 2

HCID 6329MethylamineHCID 12413149HCID 12413149, compound

Product 1

HCID 2143991-(4,5-Diphenyl-1,3-oxazol-2-yl)-N-methylmethanamine--hydrogen chloride (1/1)Yield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 22 g. 2-chloromethyl-4,5-diphenyloxazole and 12.5 g methylamine in 100 ml. anhydrous benzene was heated at 120° C for 6 hours in a sealed tube. The reaction mixture was washed with water and the separated benzene phase was distilled at 20 mm. pressure. The oily residue was dissolved in 200 ml. anhydrous ether and a flow of gas hydrogen chloride was bubbled through the resulting solution. The 2-methylaminomethyl-4,5-diphenyloxazole hydrochloride was recrystallized from absolute ethanol: 16.5 g., m.p. 207°-208° C (yield 69%).

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 200 ml
  4. customanhydrous ether and a flow of gas hydrogen chloride was bubbled through the resulting solution
  5. customThe 2-methylaminomethyl-4,5-diphenyloxazole hydrochloride was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-7b860d0adfc641158a5936b340f9b777
Source dataset
uspto-grants-1977_04
Patent number
US04020082

Reaction notes

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