2,6-Dimethylaniline → HCID 15680270, compound

HRID 1460639Notes

Reaction equation

HRID 1460639 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×

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. Analysis calc. for C27H39NO2S(441.67): Calc.: C, 73.43; H, 8.90; N, 3.17; S, 7.26. Found: C, 73.75; H, 8.90; N, 3.12; S, 7.41.

Workup

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

Sources & evidence

ORD record
ord-dcb9770c757f4499b4b3c71da64c7313
Source dataset
uspto-grants-1991_12
Patent number
US05071876

Reaction notes

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