Dimethylformamide → HCID 12788557, compound

HRID 426688Notes

Reaction equation

HRID 426688 reaction equation
[CH3:1]/[C:2](/[CH:7]=[CH:8]/[C:9](/[F:22])=[C:10](\[CH3:21])/[CH:11]=[CH:12]/[C:13]1[C:17]([CH3:18])=[C:16]([CH3:19])[S:15][C:14]=1[CH3:20])=[CH:3]\[C:4]([OH:6])=O.C[N:24]([CH3:27])C=O.[C:28](Cl)(=O)C(Cl)=O>C1C=CC=CC=1>[CH2:27]([NH:24][C:4](=[O:6])/[CH:3]=[C:2](\[CH3:1])/[CH:7]=[CH:8]/[C:9](/[F:22])=[C:10](\[CH3:21])/[CH:11]=[CH:12]/[C:13]1[C:17]([CH3:18])=[C:16]([CH3:19])[S:15][C:14]=1[CH3:20])[CH3:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 12788553HCID 12788553, compound

Product 1

HCID 12788557HCID 12788557, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A suspension of 0.25 g. (0.78 mmole) of 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraenoic acid in 15 ml. of dry benzene was stirred at 23° C. under argon while about 5 mg. of dimethylformamide were added thereto followed by 0.20 g. (1.57 mmole) of oxalylchloride in 5 ml. of dry benzene. After one hour of stirring, dry ethylamine was bubbled into the resulting orange solution until a bright yellow color persisted. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried with magnesium sulfate, filtered and evaporated to give a crude orange solid. This material was purified by chromatography on silica gel using ethyl acetate-hexane (1:1 parts by volume) as elutant. One crystallization from ethyl acetate-hexane (1:1 parts by volume) gave 130 mg. (48% yield) of pure N-ethyl (2E,4E,6Z,8E)-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraenamide, m.p. 167°-171° C.

Workup

  1. additionA suspension of 0.25 g
  2. customdry ethylamine was bubbled into the resulting orange solution until a bright yellow color
  3. additionThe reaction mixture was poured into water
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a crude orange solid
  10. customThis material was purified by chromatography on silica gel
  11. customOne crystallization from ethyl acetate-hexane (1:1 parts by volume)
  12. customgave 130 mg

Sources & evidence

ORD record
ord-1cdbfd36e91f442db849bee5e60b7af8
Source dataset
uspto-grants-1979_10
Patent number
US04171318

Reaction notes

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