Dimethylformamide → HCID 12788557, compound

HRID 1156433Notes

Reaction equation

HRID 1156433 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-24ab21cdcceb41afb99ab3d351014f4c
Source dataset
uspto-grants-1982_06
Patent number
US04335248

Reaction notes

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