HCID 11046378, compound → HCID 10970290, compound

HRID 1824589Notes

Reaction equation

N[C:2]1[C:3]([Cl:23])=[CH:4][C:5]([N+:20]([O-:22])=[O:21])=[C:6]([S:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH:7]=1.N([O-])=O.[Na+].[F:28][P-](F)(F)(F)(F)F.[H+]>Cl>[Cl:23][C:3]1[C:2]([F:28])=[CH:7][C:6]([S:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 2-(5-amino-4-chloro-2-nitro-phenylthio)-N,N-dimethyl-benzamide (18) (1 g, 2.84 mmol) in 6 N HCl (10 mL), a solution of sodium nitrite (0.3 g, 4.35 mmol) in wter (0.5 mL) was added at −5° C. (−0° C.). To this mixture, 48% hexafluorophosphoric acid (1.5 mL) was added at 0° C. and the mixture was stirred for 10 min. The precipitate was collected by filtration. The deep red solid was washed with ice water and air-dried using suction filter. The solid was further dried under high vacuum for several hours. The red powder was heated at 170° C. using oil bath until gas evolution was no longer observed. Dark colored residue was purified by silica gel chromatography to yield 380 mg of (19) (37%). IR (cm−1, neat) 2927, 1634, 1521, 1465, 1400, 1336, 1282, 1249, 1091, 1H NMR (200 MHz CDCl3) δ 8.32 (d, J=2.8 Hz, 1H), 7.4–7.6 (m, 4H), 6.67 (d, J=5.0 Hz, 1H), 3.04 (s, 3H), 2.84 (s, 3H). Anal. (C15H12ClFN2O3S) C, H, N.

Workup

filtrationThe precipitate was collected by filtration
washThe deep red solid was washed with ice water
customair-dried
filtrationfilter
customThe solid was further dried under high vacuum for several hours
customDark colored residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-abea198e52674638a9fbf8aa68e8b991
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041851B2

Reaction notes

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