Dimethyl Sulfide → HCID 21912234, compound

HRID 2307982Notes

Reaction equation

HRID 2307982 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[C:12]([C:13](O)=[O:14])=[C:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:10]=[C:9]([CH3:25])[CH:8]=1)[CH2:4][CH3:5])[CH3:2].CSC>C1COCC1>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:11]1[C:12]([CH2:13][OH:14])=[C:7]([O:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:8]=[C:9]([CH3:25])[N:10]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 21912362HCID 21912362, compound

Product 1

HCID 21912234HCID 21912234, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-ethyl-propoxy)-6-methyl-2-(2,4-dichloro-phenylamino)-nicotinic acid in dry THF was added BH3.DMS. The resulting mixture was heated at reflux overnight. The mixture was quenched with dilute HCl and stirred for 30 min, adjusted pH to 7.5-8.5, then extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a golden oil. After silica gel column chromatography, the title compound was obtained as a golden oil. 1H NMR(CDCl3) d 8.44(d,1H), 8.18(s,1H), 7.32(d,1H), 7.179d,1H), 6.28(s,1H), 4.82(s,2H), 4.21(m,1H), 2.42(s,3H), 1.6-1.8(m,4H), 0.94(t,6H) ppm.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customThe mixture was quenched with dilute HCl
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customto give a golden oil

Sources & evidence

ORD record
ord-50d1c24e895c4285897c91144e0e96e1
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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