Benzyl Bromide → Ethyl 5-(3-benzyl-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

HRID 560688Notes

Reaction equation

HRID 560688 reaction equation
FC(F)(F)[C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.C(Br)C1C=CC=CC=1.[CH3:21][C:22]1[CH:26]=[C:25]([N:27]2[CH2:31][CH2:30][NH:29][C:28]2=[O:32])[S:24][C:23]=1[C:33]([O:35][CH2:36][CH3:37])=[O:34]>>[CH2:7]([N:29]1[CH2:30][CH2:31][N:27]([C:25]2[S:24][C:23]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:22]([CH3:21])[CH:26]=2)[C:28]1=[O:32])[C:6]1[CH:5]=[CH:4][CH:3]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 58031554Ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 58031603Ethyl 5-(3-benzyl-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylateYield 94%

Procedure

Following the procedure as described in Example 13, making variations as required to replace 4-(trifluoromethyl)benzyl bromide with benzyl bromide to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as a colorless solid in 94% yield: 1H NMR (300 MHz, CDCl3) δ 7.39-7.25 (m, 5H), 6.15 (s, 1H), 4.48 (s, 2H), 4.28 (q, J=7.1 Hz, 2H), 3.83-3.75 (m, 2H), 3.48-3.40 (m, 2H), 2.49 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 345.3 (M+1).

Sources & evidence

ORD record
ord-e16c9ce7b0ba45e9b491de4c5d93da17
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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