Acetyl chloride → 4-Iodo-2-nitro-5-pyrrol-1-yl-phenylamine

HRID 1266737Notes

Reaction equation

HRID 1266737 reaction equation
[NH2:1][C:2]1[C:3]([I:15])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH:8]C(=O)C)[CH:7]=1.Cl[C:17]1[CH:18]=CC([N+]([O-])=O)=[C:21]([CH:23]=1)N.ICl.CC([O-])=O.[Na+].[N-]=[N+]=[N-].[Na+].C(Cl)(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.COC1CCC(OC)O1>CC(O)=O.CS(C)=O.C1COCC1>[I:15][C:3]1[C:2]([N:1]2[CH:21]=[CH:23][CH:17]=[CH:18]2)=[CH:7][C:6]([NH2:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

12

Reactant 8

HCID 6367Acetyl chlorideHCID 24640Iodine chlorideHCID 33557Sodium AzideHCID 742185-Chloro-2-nitroanilineHCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 18548905N-(5-amino-4-iodo-2-nitro-phenyl)-acetamideHCID 86586962Triphenylphosphine water

Product 1

HCID 185487344-Iodo-2-nitro-5-pyrrol-1-yl-phenylamine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent3×HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from N-(5-amino-4-iodo-2-nitro-phenyl)-acetamide (228 mg, 0.71 mmol) [prepared from commercially available 5-chloro-2-nitroaniline by the following sequence: i.) iodination with iodine monochloride, NaOAc in HOAc according to Wilson, J. Gerald; Hunt, Frederick C. Aust. J. Chem. 1983, 36, 2317-25; ii.) nucleophilic aromatic substitution with NaN3 in DMSO at 80° C. for 15 h; iii.) acetylation with AcCl in HOAc at 120° C. for 2 h according to Eur. J. Med. Chem. 1988, 23, 553; iv.) Staudinger-reduction with PPh3/H2O in THF at 23° C. for 1 h] and 2,5-dimethoxytetrahydrofuran (0.14 mL, 1.08 mmol) in HOAc (10 mL) at 95° C. for 2 h according to the general procedure F. Obtained as a yellow solid (221 mg). Deacetylation of this material (371 mg, 1.0 mmol) was perfomed by stirring with 1 N NaOH (2.0 mL, 2.0 mmol) in THF (3.4 mL) at 60° C. for 21 h. Obtained as a yellow solid (312 mg).

Sources & evidence

ORD record
ord-19ef03c80c4041f68ca04bfa15a049bc
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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