Chloroacetone → HCID 24765938, compound

HRID 1806024Notes

Reaction equation

HRID 1806024 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[Br:6][C:7]1[CH:8]=[C:9]([O:17][C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=2[Cl:29])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([NH:13][C:14]([NH2:16])=[S:15])=[N:11][CH:12]=1.C(N(CC)CC)C>C(O)C>[Br:6][C:7]1[CH:8]=[C:9]([O:17][C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=2[Cl:29])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([NH:13][C:14]2[S:15][CH:2]=[C:3]([CH3:4])[N:16]=2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 86631471HCID 86631471, compound

Product 1

HCID 24765938HCID 24765938, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-chloropropan-2-one (0.469 g; 5.07 mmol), ethyl 3-(5-bromo-2-thioureidopyridin-3-yloxy)-4-chlorobenzoate (1.680 g, 3.39 mmol), triethylamine (0.671 g, 6.63 mmol), and ethanol (70 mL) were reacted according to the method of Example 10, Step E, to provide the title compound (1.40 g, 77% yield). 1H NMR (d6-DMSO) δ 8.26 (d, 1H), 7.78 (m, 2H), 7.50 (s, 1H), 7.46 (d, 1H), 6.59 (s, 1H), 4.29 (q, 2H), 2.23 (s, 3H), 1.28 (t, 3H); Mass spectrum (apci) m/z=470.1 (M+H).

Sources & evidence

ORD record
ord-776b1bf799d847b0a9d278b12eae8156
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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