Tert-Butyl isocyanide → HCID 74762710, compound

HRID 1054330Notes

Reaction equation

HRID 1054330 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.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH:16]=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.O>[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:16]=1[C:15]1[CH:14]=[C:13]([Cl:12])[CH:20]=[C:19]([Cl:21])[CH:18]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 357463,5-DichlorobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 74762710HCID 74762710, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-(trifluoromethyl)pyridin-2-amine (200 mg, 1.23 mmol, Eq: 1.00), 3,5-dichlorobenzaldehyde (227 mg, 1.3 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (70.4 mg, 370 μmol, Eq: 0.3) were dissolved in MeOH (1.5 mL). The resulting colorless solution was stirred at rt. To this 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 2 h. To the yellow clear solution was added dropwise water until the mixture got turbid. After stirring for a few additional minutes, the product precipitated. The solid was filtered off, washed with MeOH/water (1:1) and with hexane and the crystals were dried under vacuum to yield a white solid (231 mg, 46.5%). MS: 402 [M]+; 1H-NMR (D6-DMSO): δ 8.91 (s, 1H), 8.30 (d, 2H), 7.73 (d, 1H), 7.57 (t, 1H), 7.49 (d, 1H), 5.05 (s, 1H), 1.07 (s, 9H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 2 h
  2. stirringAfter stirring for a few additional minutes
  3. customthe product precipitated
  4. filtrationThe solid was filtered off
  5. washwashed with MeOH/water (1:1) and with hexane
  6. customthe crystals were dried under vacuum

Sources & evidence

ORD record
ord-9aae5e9d2e5d490da2e41c7ae796483a
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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