Bromomethylcyclopropane → Ethyl 5-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

HRID 560690Notes

Reaction equation

HRID 560690 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][CH:15]1[CH2:17][CH2:16]1.[CH3:18][C:19]1[CH:23]=[C:22]([N:24]2[CH2:28][CH2:27][NH:26][C:25]2=[O:29])[S:21][C:20]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH:17]1([CH2:16][N:26]2[CH2:27][CH2:28][N:24]([C:22]3[S:21][C:20]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:19]([CH3:18])[CH:23]=3)[C:25]2=[O:29])[CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 58031554Ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 58031615Ethyl 5-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylateYield 80%

Procedure

Following the procedure as described in Example 13, making variations as required to replace 4-(trifluoromethyl)benzyl bromide with (bromomethyl)cyclopropane to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as a colorless solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 6.14 (s, 1H), 4.26 (q, J=7.1 Hz, 2H), 3.87-3.79 (m, 2H), 3.72-3.64 (m, 2H), 3.18 (d, J=7.1 Hz, 2H), 2.49 (s, 3H), 1.33 (t, J=7.1 Hz, 3H), 1.02-0.87 (m, 1H), 0.60-0.52 (m, 2H), 0.28-0.21 (m, 2H); MS (ES+) m/z 309.2 (M+1).

Sources & evidence

ORD record
ord-acc04235b2164b1ab03abc4109f7b47b
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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