Acetamide → 4-(4-Bromophenyl)-2-methyl-1,3-oxazole

반응식

[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=O)[CH2:7]Br)=[CH:4][CH:3]=1.[C:12]([NH2:15])(=[O:14])[CH3:13]>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:15]=[C:12]([CH3:13])[O:14][CH:7]=2)=[CH:4][CH:3]=1

참가 물질

반응물 2

HCID 178Acetamide

HCID 74544-Bromophenacyl bromide

생성물 1

HCID 128731074-(4-Bromophenyl)-2-methyl-1,3-oxazole수율 22.5%

실험 절차

4-Bromophenacyl bromide (21.3 g) and acetamide (11.3 g) were heated together at 130° C. under argon. After 2.5 h the reaction mixture was allowed to cool, and partitioned between water (150 ml) and Et2O (150 ml). The organic phase was washed with aqueous NaOH (0.5N), aqueous HCl (0.5M) and saturated aqueous NaCl solution (100 ml of each), dried (MgSO4) and evaporated to give a brown solid which was recrystallised from hexanes to give the title compound (D14) as an orange solid (4.1 g). LCMS electrospray (+ve) 239 (MH+).

후처리

temperatureto cool
custompartitioned between water (150 ml) and Et2O (150 ml)
washThe organic phase was washed with aqueous NaOH (0.5N), aqueous HCl (0.5M) and saturated aqueous NaCl solution (100 ml of each),
dry with materialdried (MgSO4)
customevaporated
customto give a brown solid which
customwas recrystallised from hexanes

출처 및 근거

ORD 기록: ord-ca041f5bd11a422190a1eca628cc90df
출처 데이터셋: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08492375B2

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