Hydrochloric Acid → HCID 22495780, compound

HRID 393539Notes

Reaction equation

[Cl:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:5]2[N:6]=[C:7](SC)[O:8][C:4]=2[CH:3]=1.[NH2:16][C:17]1[CH:22]=[C:21]([N+:23]([O-])=O)[C:20](Cl)=[CH:19]C=1O.Cl.[C:29](OCC)(=O)[CH3:30]>>[Cl:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:5]2[N:6]=[C:7]([N:23]3[CH:21]4[CH2:22][CH2:17][N:16]([CH2:19][CH2:20]4)[CH2:30][CH2:29]3)[O:8][C:4]=2[CH:3]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 8857Ethyl Acetate2×

HCID 22495791HCID 22495791, compound

HCID 2249581278827-35-7

Product 1

HCID 22495780HCID 22495780, compoundYield 74%

Procedure

The title compound was prepared from 6-chloro-2-methylsulfanyl-5-nitro-benzooxazole (prepared from 2-amino-5-chloro-4-nitrophenol by the methods described in Example 5 and Example 7) by the procedure described in Example 9 in 74% yield: 1H NMR (CDCl3, 400 MHz) δ 8.02 (d, 1H, J=2.1 Hz), 7.95 (d, 1H, J=2.1 Hz), 4.56-4.54 (m, 1H), 3.97 (t, 2H, J=5.8 Hz), 3.23-3.12 (m, 4H), 3.08-3.01 (m, 2H), 2.20-2.14 (m, 2H), 2.20-2.14(m, 2H), 1.91-1.83 (m, 2H); MS (Cl) m/z 323.1 (M+1). The hydrochloride salt was prepared by diluting in ethyl acetate and adding a 2.5 N HCl solution in ethyl acetate: mp=242.3 ° C.

Sources & evidence

ORD record: ord-18b1f289bd694519879b1f257108464e
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809094B2

Reaction notes

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