Triethylamine → HCID 57008090, compound

HRID 1953420Notes

Reaction equation

HRID 1953420 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-c43c34d4078f4e7ea559c7c8539800de
Source dataset
uspto-grants-2000_09
Patent number
US06117822

Reaction notes

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