3-Chlorobenzaldehyde → HCID 74762711, compound

HRID 1054332Notes

Reaction equation

HRID 1054332 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:33]([C:35]([CH3:38])([CH3:37])[CH3:36])#[C-:34]>CO.O>[C:35]([NH:33][C:34]1[N:6]2[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:4][C:5]2=[N:9][C:16]=1[C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 23577Tert-Butyl isocyanideHCID 521998p-Toluenesulfonic acid monohydrateHCID 27783152-Amino-4-(trifluoromethyl)pyridine

Product 1

HCID 74762711HCID 74762711, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-(trifluoromethyl)pyridin-2-amine (200 mg, 1.23 mmol, Eq: 1.00), 3-chlorobenzaldehyde (182 mg, 147 μl, 1.3 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (70.4 mg, 370 Eq: 0.3) were dissolved in MeOH (2.00 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 and the product precipitated from the MeOH/water mixture. The solid was filtered off, washed with MeOH/water (1:1) and hexane and dried under vacuum, to give a yellow solid (238 mg, 52.5%). MS: 367.0 [M]+; 1H-NMR (D6-DMSO): δ 8.63 (d, 1H), 8.29 (s, 1H), 8.18 (d, 1H), 8.00 (s, 1H), 7.49 (t, 1H), 7.40 (d, 1H), 7.15 (d, 1H), 4.95 (s, 1H), 1.04 (s, 9H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 2 h
  2. customthe product precipitated from the MeOH/water mixture
  3. filtrationThe solid was filtered off
  4. washwashed with MeOH/water (1:1) and hexane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-761ad47639db4261b301ec1b259bcc0f
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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