2-Chloroethyl isocyanate → ethyl 4-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)thiazole-5-carboxylate

HRID 560574Notes

Reaction equation

HRID 560574 reaction equation
ClCCN=C=O.Cl[CH2:8][CH2:9][CH2:10][N:11]=[C:12]=[O:13].[NH2:14][C:15]1[S:16][C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:18]([CH3:20])[N:19]=1>>[CH3:20][C:18]1[N:19]=[C:15]([N:14]2[CH2:8][CH2:9][CH2:10][NH:11][C:12]2=[O:13])[S:16][C:17]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 3

HCID 160352-Chloroethyl isocyanateHCID 166752Propane, 1-chloro-3-isocyanato-HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 58031510ethyl 4-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)thiazole-5-carboxylateYield 32%

Procedure

Following the procedure as described in Example 3, making variations as required to replace 2-chloroethyl isocyanate with 3-chloropropyl isocyanate to react with ethyl 2-amino-4-methylthiazole-5-carboxylate, the title compound was obtained as a brown solid in 32% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.21 (s, 1H), 4.75 (q, J=7.1 Hz, 2H), 4.57 (t, J=5.9 Hz, 2H), 3.80-3.75 (m, 2H), 3.05 (s, 3H), 2.54-2.46 (m, 2H), 1.81 (t, J=7.1 Hz, 3H); MS (ES+) m/z 270.2 (M+1).

Sources & evidence

ORD record
ord-f7dfd6cf876445a59d3d8e9a0a50aae6
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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