Triethylamine → HCID 57008090, compound

HRID 725793Notes

Reaction equation

HRID 725793 reaction equation
C(N1C=CN=C1)(N1[CH:7]=[CH:6]N=C1)=O.[Cl:13][C:14]1[C:19]([CH:20]=[C:21]([C:23](O)=[O:24])[Cl:22])=[CH:18][C:17]([N:26]2[C:30](=[O:31])[C:29]3[CH2:32][CH2:33][CH2:34][CH2:35][C:28]=3[C:27]2=[O:36])=[C:16]([F:37])[CH:15]=1.Cl.C([N:41]([CH2:43][C:44]([OH:46])=[O:45])[CH3:42])C.C(N(CC)CC)C>O1CCCC1>[Cl:13][C:14]1[C:19]([CH:20]=[C:21]([C:23]([N:41]([CH2:43][C:44]([O:46][CH2:6][CH3:7])=[O:45])[CH3:42])=[O:24])[Cl:22])=[CH:18][C:17]([N:26]2[C:27](=[O:36])[C:28]3[CH2:35][CH2:34][CH2:33][CH2:32][C:29]=3[C:30]2=[O:31])=[C:16]([F:37])[CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 57059430HCID 57059430, compoundHCID 867518812248417-60-7

Product 1

HCID 57008090HCID 57008090, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6 mmol of carbonyldiimidazole were added dropwise to a solution of 5 mmol of N-[4-chloro-5-(2-hydroxycarbonyl-2-chloroethen-1-yl)-2-fluorophenyl]-3,4,5,6-tetrahydrophthalimide in 50 ml of absolute tetrahydrofuran, after which stirring was carried out for one hour at about 20° C. 5 mmol of ethyl sarcosine hydrochloride were then added to the reaction mixture. 5 mmol of triethylamine in 5 ml of tetrahydrofuran were then added dropwise. Stirring was carried out for 48 hours at about 20° C., after which the solvent was removed under reduced pressure from a water-jet pump. The residue was taken up in water, after which the product was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and then evaporated down. The crude product was purified by chromatography over silica gel (eluent: 1:2 petroleum ether/methyl tert-butyl ether). Yield: 0.97 g (40%).

Workup

  1. stirringStirring
  2. waitwas carried out for 48 hours at about 20° C.
  3. customafter which the solvent was removed under reduced pressure from a water-jet pump
  4. extractionafter which the product was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated down
  7. customThe crude product was purified by chromatography over silica gel (eluent: 1:2 petroleum ether/methyl tert-butyl ether)

Sources & evidence

ORD record
ord-8e3b40eb3273490bacbf05f40dea7bc9
Source dataset
uspto-grants-1998_01
Patent number
US05707937

Reaction notes

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