Acetyl chloride → 2-Nitro-5-(3-phenyl-pyrrol-1-yl)-phenylamine

HRID 1266740Notes

Reaction equation

HRID 1266740 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH:8]C(=O)C)[CH:7]=1.ClC1C=CC([N+]([O-])=O)=C(C=1)N.[N-]=[N+]=[N-].[Na+].C(Cl)(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CO[CH:56]1[CH:60]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH2:59][CH:58](OC)O1>CS(C)=O.CC(O)=O.C1COCC1>[N+:12]([C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH:58]=[CH:59][C:60]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[CH:56]2)=[CH:7][C:6]=1[NH2:8])([O-:14])=[O:13]

Participants

10

Reactant 6

HCID 6367Acetyl chlorideHCID 33557Sodium AzideHCID 742185-Chloro-2-nitroanilineHCID 18548776N-(5-amino-2-nitro-phenyl)-acetamideHCID 185488262,5-Dimethoxy-3-phenyltetrahydrofuranHCID 86586962Triphenylphosphine water

Product 1

HCID 185488492-Nitro-5-(3-phenyl-pyrrol-1-yl)-phenylamine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from N-(5-amino-2-nitro-phenyl)-acetamide [prepared from commercially available 5-chloro-2-nitroaniline by the following sequence: i.) nucleophilic aromatic substitution with NaN3 in DMSO at 80° C. for 15 h; ii.) acetylation with AcCl in HOAc at 120° C. for 2 h according to Eur. J. Med. Chem. 1988, 23, 553; iii.) Staudinger-reduction with PPh3/H2O in THF at 23° C. for 1 h] and 2,5-dimethoxy-3-phenyl-tetrahydro-furan [CAS-no. 207119-66-2] in HOAc at 60° C. for 2 days according to the general procedure F. Obtained as a brown solid (414 mg). Deacetylation of this material was perfomed by stirring with 25% HCl in THF at 80° C. for 90 min. Obtained as a brown solid (179 mg).

Sources & evidence

ORD record
ord-a21d9d4724dc4f9ba60ada028dd1998e
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

Loading…