Dimethylformamide → HCID 12788555, compound

HRID 426689Notes

Reaction equation

HRID 426689 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](O)=[O:5].C[N:24](C)C=O.C(Cl)(=O)C(Cl)=O>C1C=CC=CC=1>[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]([NH2:24])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 12788553HCID 12788553, compound

Product 1

HCID 12788555HCID 12788555, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A suspension of 0.40 g. (0.12 mmol) of 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraenoic acid in 12 ml. of dry benzene was stirred at 23° C. under argon while about 5 mg. of dimethylformamide were added thereto followed by 0.24 g. (0.19 mmole) of oxalyl chloride in 3 ml. of dry benzene. After 1 hour of stirring, dry ammonia 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 (2:3 parts by volume) as the elutant. One crystallization from ethyl acetate gave 70 mg. (18% yield) of pure 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraenamide, m.p. 212°-215° C.

Workup

  1. additionA suspension of 0.40 g
  2. customdry ammonia 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
  12. customgave 70 mg

Sources & evidence

ORD record
ord-c74a2e10dbf24347bfda55665afe3be6
Source dataset
uspto-grants-1979_10
Patent number
US04171318

Reaction notes

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