Dimethyl Sulfoxide → N-[2-Nitro-4-fluoro-5-(methylpiperazin-1-yl)phenyl]acetamide

HRID 1004575Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7](Cl)=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14])([O-:3])=[O:2].C[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[OH-].[K+].[K+].[Br-].[CH3:27]S(C)=O>>[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[CH3:27])=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14])([O-:3])=[O:2]

Participants

Reactant 5

HCID 679Dimethyl Sulfoxide

HCID 14797Potassium Hydroxide

HCID 531671-Methylpiperazine

HCID 253877Potassium Bromide

HCID 2773811N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide

Product 1

HCID 18792798N-[2-Nitro-4-fluoro-5-(methylpiperazin-1-yl)phenyl]acetamideYield 80%

Procedure

N-[2-Nitro-4-fluoro-5-(methylpiperazin-1-yl)phenyl]acetamide (25.0 g, 80%) was prepared by an analogous procedure as described in preparation 1 (step 3) using N-(2-nitro-4-fluoro-5-chlorophenyl)acetamide (25.0 g, 0.107 mol) (obtained in preparation 1, step 2), 4-methylpiperazine (53.5 g, 0.535 mol), potassium hydroxide (9.05 g, 0.16 mol) and dimethyl sulfoxide (100 mL). mp 90-91° C.; IR (KBr) 3339, 1707, 1582 cm-1 ; 1H NMR (CDCl3) δ 2.24 (s, 3H, CH3), 2.32 (s, 3H, CH3), 2.56 (t, J=5.0 Hz, 4H, N(CH2)2), 3.42 (t, J=5.0 Hz, 4H, N(CH2)2), 7.90 (d, J=14.1 Hz, 1H), 8.36 (d, J=8.4 Hz, 1H), 10.70 (brs, 1H, NH); Mass (m/z) 296 (M+.).

Workup

customas described in preparation 1 (step 3)

Sources & evidence

ORD record: ord-e73b184e09a54752a572a248c7e4e589
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06051570

Reaction notes

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