Tert-Butyl isocyanide → HCID 74763782, compound

HRID 1054325Notes

Reaction equation

HRID 1054325 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH:9]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:31]([C:33]([CH3:36])([CH3:35])[CH3:34])#[C-:32]>CO>[C:33]([NH:31][C:32]1[N:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:8][C:9]=1[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15])([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 661742-Amino-5-chloropyridineHCID 90670m-FormylbenzonitrileHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 74763782HCID 74763782, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-chloropyridin-2-amine (200 mg, 1.56 mmol, Eq: 1.00), 3-formylbenzonitrile (214 mg, 1.63 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (88.8 mg, 467 μmol, Eq: 0.3) were dissolved in MeOH (2.00 mL) and the intensive yellow solution was stirred for 10 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (129 mg, 177 μL, 1.56 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 80 min whereupon a white precipitate was formed. The precipitate was filtered off, washed with MeOH (4 mL) and dried under vacuum to give the product as a white solid (351 mg, 69.5%). MS: 325.2 [M+H]+; 1H-NMR (D6-DMSO): δ 8.59 (m, 2H), 8.49 (d, 1H), 7.78 (d, 1H), 7.65 (t, 1H), 7.58 (d, 1H), 7.29 (dd, 1H), 4.88 (s, 1H), 1.02 (s, 9H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 80 min whereupon a white precipitate
  2. customwas formed
  3. filtrationThe precipitate was filtered off
  4. washwashed with MeOH (4 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2749a4de7f4d46e7bdd7b09eea0bccfc
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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