2-Acetamidothiazole → 2-[(2-chloro-1-oxo-3-methylbutyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-(trifluoromethyl)-benzene propanamide

HRID 704755Notes

Reaction equation

HRID 704755 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:20]1[O:25][C:24](=[O:26])[C:23]2[CH:27]=[CH:28][CH:29]=[C:30]([C:31]([F:34])([F:33])[F:32])[C:22]=2[N:21]=1)[CH:17]([CH3:19])[CH3:18]>CCCCCC.O1CCCC1>[Cl:15][CH:16]([CH:17]([CH3:19])[CH3:18])[C:20]([NH:21][C:22]1[C:30]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](=[O:26])[CH2:8][C:7]([NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[O:9])=[O:25]

Participants

6

Reactant 3

HCID 176252-AcetamidothiazoleHCID 136556172-(1-chloro-2-methylpropyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-oneHCID 178418339Butyllithium

Product 1

HCID 134230872-[(2-chloro-1-oxo-3-methylbutyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-(trifluoromethyl)-benzene propanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

10.6 g of N-(2-thiazolyl)-acetamide, 325 ml of tetrahydrofuran and 106 ml of n-butyllithium in hexane titrating 1.4 M and 11.4 g of 2-(1-chloro-2-methylpropyl)-8-(trifluoromethyl)-4H-3, benzoxazin-4-one of Step A in solution in 80 ml of tetrahydrofuran were reacted by the procedure of Step A of Example 6 of Belgian Patent No. 896,941 to obtain 13.8 g of 2-[(2-chloro-1-oxo-3-methylbutyl)-amino]-β-oxo-N-(2-thiazolyl)-3-(trifluoromethyl)-benzene propanamide melting at 186° C.

Sources & evidence

ORD record
ord-752e0e708d2d4f85a8a86d939e93b354
Source dataset
uspto-grants-1991_01
Patent number
US04988708

Reaction notes

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