Ethyl 4-chloroacetoacetate → HCID 13500406, compound

HRID 1642399Notes

Reaction equation

HRID 1642399 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[Cl:9][CH2:10][C:11](=O)[CH2:12][C:13](OCC)=[O:14].C1(COC2C(OC)=CC=CC=2/C=C/C2N=C3SC=CN3C(=O)C=2I)CC1>>[Cl:9][CH2:10][C:11]1[N:1]=[C:2]2[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]2[C:13](=[O:14])[CH:12]=1

Participants

4

Reactant 3

HCID 69484Ethyl 4-chloroacetoacetateHCID 732382-Amino-4,5-dimethyl-1,3-thiazoleHCID 66753592HCID 66753592, compound

Product 1

HCID 13500406HCID 13500406, compoundYield 144%

Procedure

This compound was synthesized from 2-amino-4,5-dimethylthiazole (5.0 g, 30.365 mmol) and ethyl chloroacetoacetate (6.519 g, 42.511 mmol) in polyphosphoric acid (40.0 g) according to the procedure described in Step 1, Intermediate 2 to afford 10.0 g of the desired compound as a black solid; 1H NMR (300 MHz, DMSO-d6) δ 2.28 (s, 3H), 2.60 (s, 3H), 4.52 (s, 1H), 6.25 (s, 1H); ESI-MS (m/z) 229.60 (M+H)+.

Sources & evidence

ORD record
ord-a78345cc7e4b402fa79956fd0f679d55
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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