4-(Trifluoromethyl)benzenesulfonyl chloride → HCID 18958010, compound

HRID 2225461Notes

Reaction equation

HRID 2225461 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[O:13][CH:12]([CH3:14])[NH:11][CH2:10]1.[F:21][C:22]([F:34])([F:33])[C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[O:13][CH:12]([CH3:14])[N:11]([S:29]([C:26]2[CH:25]=[CH:24][C:23]([C:22]([F:21])([F:33])[F:34])=[CH:28][CH:27]=2)(=[O:31])=[O:30])[CH2:10]1

Participants

3

Reactant 2

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 18957991HCID 18957991, compound

Product 1

HCID 18958010HCID 18958010, compound

Procedure

Following the general sulfonylation procedure explained in example 1 but using 5-(2,4-dichlorophenyl)-2-methyl-5-[(1H-1,2,4-triazol-1-yl]methyl)oxazolidine, obtained according to patent ES 334509/91 and 4-trifluoromethylbenzenesulfonyl chloride, the title product is obtained in similar yield as a single isomer. mp 188°-190° C. 1H NMR (80 MHz, CDCl3)δ(TMS) 8.06 (s, 1H, N=CH), 7.80 (s, 1H, N=CH), 7.7-7.2 (m, 5H, arom), 7.02 (s, 2H, arom), 5.20 (q, J=5.3 Hz, 1H, CHMe), 4.60 (AB system, Δv=0.32, J=14.6 Hz, 2H, CH2 -Tr), 4.13 (AB system, Δv=0.62, J=12 Hz, 2H, NCH2), 1.49 (d, J=5.3 Hz, 3H, CHMe). Anal. calcd. for C20H17F3Cl2N4O3S: C 46.08%; H 3.29%; N 10.75%. Found: C 46.34%; H 3.54%; N 10.43%.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-d174a4b0157d432f910a4e981c87f868
Source dataset
uspto-grants-1994_09
Patent number
US05344839

Reaction notes

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