Ethyl cyanoacetate → HCID 69779882, compound

HRID 1266723Notes

Reaction equation

HRID 1266723 reaction equation
[N-]=[C:2]=O.[NH2:4][C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[CH:7][C:8]([I:14])=[C:9]([CH2:11][C:12]#[N:13])[CH:10]=1.ClC1C=C[C:22]([N+]([O-])=O)=[C:23](N)[CH:24]=1.ICl.C[C:32]([O-:34])=[O:33].[Na+].C(CC(OCC)=O)#N.[Li+].[Cl-].O.O=C(Cl)OC(Cl)(Cl)Cl>CC(O)=O.CS(C)=O.CCOC(C)=O.C(Cl)Cl.C(O)CCC>[C:23]([O:34][C:32](=[O:33])[NH:4][C:5]1[CH:10]=[C:9]([CH2:11][C:12]#[N:13])[C:8]([I:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])([CH3:22])([CH3:24])[CH3:2]

Participants

13

Reactant 7

HCID 7764Ethyl cyanoacetateHCID 10426DiphosgeneHCID 742185-Chloro-2-nitroanilineHCID 105034IsocyanateHCID 18548899HCID 18548899, compoundHCID 23681138Lithium chloride hydrateHCID 131723860HCID 131723860, compound

Product 1

HCID 69779882HCID 69779882, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 2631-ButanolSolventHCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared via the isocyanate from (5-amino-2-iodo-4-nitro-phenyl)-acetonitrile [prepared from 5-chloro-2-nitro-phenylamine by: i.) iodination with ICl/NaOAc in HOAc at 60° C.; ii.) reaction with ethyl cyanoacetate and KOBut in DMSO at 100° C. for 2 h.; iii.) deacarboxylation with LiCl/H2O in DMSO at 120° C. for 2.5 h] (5.15 g, 17 mmol) and diphosgene (2.05 mL, 17 mmol) in EtOAc (150 mL), followed by treatment with tert.-BuOH (25 mL) in CH2Cl2 (25 mL) according to the general procedure A (method a). Obtained as a yellow solid (4.00 g).

Workup

  1. customat 60° C.

Sources & evidence

ORD record
ord-e1080ddc7f3449e0a43a7b78e8f2acd1
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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