Toluene → HCID 66856099, compound

HRID 2402448Notes

Reaction equation

HRID 2402448 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]([I:22])=[C:10]([C:20]#[N:21])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])=O.C1(C)C=CC=CC=1.P(Cl)(Cl)(Cl)=O>>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:11]1[C:10]([C:20]#[N:21])=[C:9]([I:22])[S:8][C:7]=1[C:5]1[NH:4][CH2:3][CH2:2][N:1]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 66855620HCID 66855620, compound

Product 1

HCID 66856099HCID 66856099, compoundYield 89.6%

Conditions

Temperature
120 °C

Procedure

To a mixture of N-(2-aminoethyl)-4-cyano-3-(2,4-dichlorophenyl)-5-iodothiophene-2-carboxamide (1.16 g, 0.00249 mol) in Toluene (20 mL, 0.19 mol) in a pressure vessel was added Phosphoryl chloride (2.0 mL, 0.022 mol) and the mixture was heated at 120° C. for 3 hours. Solvent was evaporated and the residue was diluted with water, treated with 1N NaOH (10 mL) and extracted with DCM (5×50 mL). The combined DCM layers were washed with brine, dried with MgSO4, filtered and concentrated to afford the product (1.00 g, 89%). LCMS: (FA) ES+, 448, 450. 1H NMR (400 MHz, d6-DMSO) δ: 7.81-7.78 (m, 1H) 7.56-7.52 (m, 1H), 7.50-7.47 (m, 1H), 3.67-3.59 (m, 2H), 3.25-3.17 (m, 2H).

Workup

  1. customSolvent was evaporated
  2. additionthe residue was diluted with water
  3. additiontreated with 1N NaOH (10 mL)
  4. extractionextracted with DCM (5×50 mL)
  5. washThe combined DCM layers were washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-50a7b8276f5242b89f8fe8127c7dec91
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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