2-(Trifluoromethyl)benzoyl chloride → Propyl 4,4,6,6-tetramethyl-2-{[2-(trifluoromethyl)benzoyl]amino}-4,6-dihydrothieno[2,3-c]furan-3-carboxylate

HRID 1015603Notes

Reaction equation

HRID 1015603 reaction equation
[NH2:1][C:2]1[S:13][C:5]2[C:6]([CH3:12])([CH3:11])[O:7][C:8]([CH3:10])([CH3:9])[C:4]=2[C:3]=1[C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15].[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>>[CH3:10][C:8]1([CH3:9])[O:7][C:6]([CH3:11])([CH3:12])[C:5]2[S:13][C:2]([NH:1][C:24](=[O:25])[C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[C:21]([F:20])([F:31])[F:32])=[C:3]([C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15])[C:4]1=2

Participants

3

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 67300643Propyl 2-amino-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxylate

Product 1

HCID 24772680Propyl 4,4,6,6-tetramethyl-2-{[2-(trifluoromethyl)benzoyl]amino}-4,6-dihydrothieno[2,3-c]furan-3-carboxylate

Procedure

The title compound was prepared from the product of Example 62A and commercially available 2-trifluoromethylbenzoyl chloride using the procedure described for Example 1B. 1H NMR (DMSO-d6, 300 MHz) δ 0.90 (t, J=7.5 Hz, 3H), 1.50 (s, 6H), 1.54 (s, 6H), 1.63-1.75 (m, 2H), 4.22 (t, J=6.8 Hz, 2H), 7.79-7.95 (m, 4H), 11.47 (br s, 1H). MS (ESI+) m/z 456 (M+H)+. Anal. calcd. for C22H24F3NO4S: C, 58.01; H, 5.31; N, 3.08. Found: C, 57.97; H, 5.37; N, 3.04.

Sources & evidence

ORD record
ord-7bebc134bded43d1b18da54d3b6d334f
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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