Formaldehyde → HCID 178440757, compound

HRID 1612591Notes

Reaction equation

HRID 1612591 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]=1[OH:22])([CH3:11])([CH3:10])[CH3:9].C=O.[CH2:25](NCCCC)CCC>C(O)C>[C:18]([C:14]1[CH:15]=[C:16]([CH:17]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:13]=1[OH:22])[CH2:25][C:4]1[CH:3]=[C:2]([SH:1])[CH:7]=[CH:6][N:5]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8148DibutylamineHCID 314052,6-Di-tert-butylphenolHCID 178418431pyridine-4-thiol

Product 1

HCID 178440757HCID 178440757, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

4-Mercaptopyridine (11.1 g, 0.1 mol), 2,6-di-tertbutylphenol (20,6 g, 0.1 mol), paraformaldehyde (3.0 g, 0.1M) and di-n-butylamine (1 ml) are heated at 80° C. for two and half hours, after which time, thin layer chromatography (t.l.c.) showed the reaction to be complete. The reaction mixture is cooled to 50° C., ethanol (100 ml) is added and the product is crystallised as a pale yellow solid (24.7 g, 78.4% of theory) of m.p. 169°-171° C. (Found C=73.30; H=8.49; N=4.31; S=9.71 C20H27NOS requires C=72.95; H=8.21; N=4.26 and S=9.73%).

Workup

  1. customthe reaction
  2. customthe product is crystallised as a pale yellow solid (24.7 g, 78.4% of theory) of m.p. 169°-171° C. (Found C=73.30; H=8.49; N=4.31; S=9.71 C20H27NOS requires C=72.95; H=8.21; N=4.26 and S=9.73%)

Sources & evidence

ORD record
ord-e57284cf975f446288dee76b646703fd
Source dataset
uspto-grants-1993_03
Patent number
US05190723

Reaction notes

Loading…