2-Chloroethyl isocyanate → Methyl 2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

HRID 560571Notes

Reaction equation

HRID 560571 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11]C)=[O:9])=[C:5](C)[N:6]=1.NC1SC(C(OC)=O)=CN=1.Cl[CH2:24][CH2:25][N:26]=[C:27]=[O:28]>>[O:28]=[C:27]1[NH:26][CH2:25][CH2:24][N:1]1[C:2]1[S:3][C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][N:6]=1

Participants

4

Reactant 3

HCID 160352-Chloroethyl isocyanateHCID 238005Methyl 2-aminothiazole-5-carboxylateHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 58031476Methyl 2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylateYield 44%

Procedure

Following the procedure as described in Example 3, making variations as required to replace ethyl 2-amino-4-methylthiazole-5-carboxylate with methyl 2-aminothiazole-5-carboxylate to react with 2-chloroethyl isocyanate, the title compound was obtained as a colorless solid in 44% yield: mp 205-208° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.02 (s, 1H), 5.55 (s, 1H), 4.25-4.19 (m, 2H), 3.84 (s, 3H), 3.72-3.67 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.8, 162.5, 157.0, 145.1, 122.2, 52.1, 44.4, 38.1; MS (ES+) m/z 228.2 (M+1).

Sources & evidence

ORD record
ord-f177af84efcb47b3a5f2dbb48ed7d2a8
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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