2,6-Dimethylaniline → HCID 15680270, compound

HRID 483452Notes

Reaction equation

HRID 483452 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH:17]([CH2:21][CH2:22][CH3:23])[C:18](O)=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C(Cl)(=O)C(Cl)=O.[CH3:30][C:31]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:32]=1[NH2:33].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:13][C:12]([C:9]1[CH:8]=[C:7]([S:16][CH:17]([CH2:21][CH2:22][CH3:23])[C:18]([NH:33][C:32]2[C:34]([CH3:38])=[CH:35][CH:36]=[CH:37][C:31]=2[CH3:30])=[O:19])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:4])[CH3:3])[C:10]=1[OH:11])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15680272HCID 15680272, compound

Product 1

HCID 15680270HCID 15680270, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Conditions

Temperature
10 °C

Procedure

The title compound of Example 11 (2.3 g, 0.0068 mole) was dissolved in benzene and the solution cooled to 10° C. in an ice bath. A solution of oxalyl chloride (1.14 g, 0.009 mole) in benzene (10 ml) was added dropwise over a period of 20 minutes. The ice bath was removed and the solution stirred at room temperature for 12 hours. The benzene was removed, fresh benzene (10 ml) added and the procedure repeated. The residue was taken up in benzene and a solution of 2,6-dimethylaniline (0.84 g, 0.007 mole) in benzene (25 ml) added over a period of 20 minutes, followed by the dropwise addition of a solution of triethylamine (1 ml). The solution was stirred for 4 hours and the benzene removed. The residue was taken up in ethyl ether (100 ml), stirred, and the white solid filtered. The filtrate was stripped and the product purified by chromatography on silica. The product was recrystallized from ethyl acetate/hexane, filtered and dried, m.p. ca. 137°-139.5° C.

Workup

  1. customThe ice bath was removed
  2. customThe benzene was removed
  3. additionfresh benzene (10 ml) added
  4. stirringThe solution was stirred for 4 hours
  5. customthe benzene removed
  6. stirringstirred
  7. filtrationthe white solid filtered
  8. customthe product purified by chromatography on silica
  9. customThe product was recrystallized from ethyl acetate/hexane
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-4783cba7435849d1a13b26d8616ffaf8
Source dataset
uspto-grants-1993_07
Patent number
US05225444

Reaction notes

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