2-Acetamidothiazole → 2-[(2-chloro-1-oxo-butyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-trifloromethyl-benzenepropanamide

HRID 648753Notes

Reaction equation

HRID 648753 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:9])[CH3:8].C([Li])CCC.[Cl:15][CH:16]([C:19]1[O:24][C:23](=[O:25])[C:22]2[CH:26]=[CH:27][CH:28]=[C:29]([C:30]([F:33])([F:32])[F:31])[C:21]=2[N:20]=1)[CH2:17][CH3:18]>O1CCCC1.CCCCCC>[Cl:15][CH:16]([CH2:17][CH3:18])[C:19]([NH:20][C:21]1[C:29]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](=[O:25])[CH2:8][C:7]([NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[O:9])=[O:24]

Participants

6

Reactant 3

HCID 176252-AcetamidothiazoleHCID 134230814H-3,1-Benzoxazin-4-one, 2-(1-chloropropyl)-8-(trifluoromethyl)-HCID 178418339Butyllithium

Product 1

HCID 134230842-[(2-chloro-1-oxo-butyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-trifloromethyl-benzenepropanamideYield 21.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Using the procedure of Step A of Example 6, a solution of 16.58 g of N-(2-thiazolyl)-acetamide in 340 ml of tetrahydrofuran, 155 ml of a solution of butyllithium in hexane and a solution of 17 g of the product of Step A in 170 ml of tetrahydrofuran were reacted to obtain 5.5 g of 2-[(2-chloro-1-oxo-butyl)-amino]-β-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzenepropanamide melting at 170° C.

Sources & evidence

ORD record
ord-18e8bb7d26f04a9aa542e0c2318c631c
Source dataset
uspto-grants-1988_04
Patent number
US04736033

Reaction notes

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