Diiodomethane → HCID 59250036, compound

HRID 1926625Notes

Reaction equation

HRID 1926625 reaction equation
N[C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:3]=1[C:20]#[N:21].[I:22]CI.N(OCCC(C)C)=O>C(#N)C>[C:20]([C:3]1[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:6][C:2]=1[I:22])#[N:21]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 59250010HCID 59250010, compound

Product 1

HCID 59250036HCID 59250036, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
38 °C

Procedure

To a suspension of ethyl 5-amino-4-cyano-3-(2,4-dichlorophenyl)thiophene-2-carboxylate (2.92 g, 0.00856 mol) in acetonitrile (10 mL) was added diiodomethane (2.41 mL, 0.0300 mol) under an atmosphere of argon and was heated at 38° C. Isoamyl nitrite (2.61 g, 0.0214 mol) was added dropwise and the reaction mixture was cooled to room temperature and stirred for one hour. The reaction was concentrated in vacuo and column chromatography was performed to yield the title compound (1.44 g, 37%) as an orange solid. 1H NMR (400 MHz, d1-chloroform) δ: 7.53 (d, 1H, J=2.00 Hz), 7.38-7.34 (m, 1H), 7.21 (d, 1H, J=8.28 Hz), 4.25-4.15 (m, 2H), 1.21-1.16 (m, 3H).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationThe reaction was concentrated in vacuo and column chromatography

Sources & evidence

ORD record
ord-eedb09bbae8446e6aae87cc52cbc8030
Source dataset
uspto-grants-2012_05
Patent number
US08183240B2

Reaction notes

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