Tert-Butyl isocyanide → HCID 74763781, compound

HRID 1054324Notes

Reaction equation

HRID 1054324 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[CH:12]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:34]([C:36]([CH3:39])([CH3:38])[CH3:37])#[C-:35]>CO>[C:36]([NH:34][C:35]1[N:7]2[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=[CH:5][C:6]2=[N:9][C:12]=1[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 90670m-FormylbenzonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 74763781HCID 74763781, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(trifluoromethyl)pyridin-2-amine (200 mg, 1.23 mmol, Eq: 1.00), 3-formylbenzonitrile (170 mg, 1.3 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (70.4 mg, 370 μmol, Eq: 0.3) were dissolved in MeOH (2.00 mL) and the intensive yellow solution was stirred for 20 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (103 mg, 140 μL, 1.23 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 1 h 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 an off-white solid (120 mg, 27.1%). MS: 359.2 [M+H]+; 1H-NMR (D6-DMSO): δ 8.91 (s, 1H), 8.64 (s, 1H), 8.54 (d, 1H), 7.81 (d, 1H), 7.74 (d, 1H), 7.68 (t, 1H), 7.48 (dd, 1H), 5.03 (s, 1H), 1.03 (s, 9H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 1 h 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-551b197bc0c24c91b2df371a3f226dc8
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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