Diisopropylaniline → HCID 178439041, compound

HRID 1944835Notes

Reaction equation

HRID 1944835 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:29]=[CH:28][CH:27]=[CH:26][C:10]=2[CH2:11][N:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:5][CH:4]=1)=O.[CH:30]([C:33]1[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]([CH3:42])[CH3:41])[C:34]=1[NH2:35])([CH3:32])[CH3:31].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[CH:40]([C:36]1[CH:37]=[CH:38][CH:39]=[C:33]([CH:30]([CH3:32])[CH3:31])[C:34]=1/[N:35]=[CH:1]/[C:3]1[N:8]=[C:7]([C:9]2[CH:29]=[CH:28][CH:27]=[CH:26][C:10]=2[CH2:11][N:12]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH:6]=[CH:5][CH:4]=1)([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 32484DiisopropylanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 58434438tert-Butyl 2-(6-formylpyridin-2-yl)benzyl(phenyl)carbamate

Product 1

HCID 178439041HCID 178439041, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

Tetrahydrofuran (50 mL) and 4 angstrom molecular sieves (ca. 15 mL) were added to tert-butyl 2-(6-formylpyridin-2-yl)benzyl(phenyl)carbamate (11) (03.63 g, 9.34 mmol). Then 2,6-diisopropylaniline (1.66 g, 9.34 mmol) was added followed by a catalytic amount of p-toluenesulfonic acid monohydrate (0.003 g, 0.015 mmol). The mixture was stirred overnight then filtered and evaporated to a thick yellow oil. After several days the oil began to crystallize. Methanol (40 mL) was added and the mixture was stirred to give a yellow crystalline solid. The mixture was cooled to 5° C. for a couple of hours then the solid was collected on a glass fit and dried under reduced pressure. Yield: 3.93 g, 76.8%. 1H NMR (CD2Cl2, 500 MHz): 8.26 (s, 1H), 8.19 (d, 1H), 7.87 (t, 1H), 7.54 (d, 1H), 7.32-7.42 (m, 4H), 7.02-7.20 (m, 8H), 5.11 (s, 2H), 2.99 (sept, 2H), 1.34 (s, 9H), 1.18 (d, 12H).

Workup

  1. filtrationthen filtered
  2. customevaporated to a thick yellow oil
  3. waitAfter several days the oil began
  4. customto crystallize
  5. additionMethanol (40 mL) was added
  6. stirringthe mixture was stirred
  7. customto give a yellow crystalline solid
  8. customthe solid was collected on a glass fit
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-5478a0da402b477298c73ef2b3c03b43
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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