Formaldehyde → HCID 15324506, compound

HRID 1885808Notes

Reaction equation

HRID 1885808 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([SH:12])[CH:9]=[C:8]([CH3:13])[C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].[C:14]1([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:27]=O>CO>[NH2:7][C:6]1[C:8]([CH3:13])=[CH:9][C:10]([S:12][CH2:27][N:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:11][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11487DiphenylamineHCID 153245012-Tert-butyl-4-mercapto-6-methylaniline

Product 1

HCID 15324506HCID 15324506, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4.5 g (23 mmol) of 2-tert-butyl-4-mercapto-6-methylaniline and 3.9 g (23 mmol) of diphenylamine in 30 mL of methanol at -5° C. is added 0.9 g (23 mmol) of formaldehyde as a 37% aqueous solution (1.9 mL). The reaction mixture is stirred for 72 hours at room temperature and then is heated for 5 hours at 50°-55° C. The solvent is removed in vacuo and the residue is purified by flash column chromatography (silica gel, 9:1, heptane:ethyl acetate eluent) to give 3.9 g (45%) of the title compound as a colorless liquid.

Workup

  1. temperatureis heated for 5 hours at 50°-55° C
  2. customThe solvent is removed in vacuo
  3. customthe residue is purified by flash column chromatography (silica gel, 9:1, heptane:ethyl acetate eluent)

Sources & evidence

ORD record
ord-9b43a6801cb24190bd886be7d0542e3d
Source dataset
uspto-grants-1992_09
Patent number
US05145970

Reaction notes

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