Heptanoic Acid → HCID 19100373, compound

HRID 2254497Notes

Reaction equation

HRID 2254497 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:23](O)(=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>O1CCCC1.C(Cl)Cl>[CH2:24]([C:23]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1)=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 8094Heptanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 135736970HCID 135736970, compound

Product 1

HCID 19100373HCID 19100373, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.32 g (1.03 mM) of 2-(p-hydroxyphenyl)-6-hexylbenzothiazole, 0.13 g 1.03 mM) of heptanoic acid, 15 ml of methylene chloride and 5 ml of tetrahydrofuran were added, followed by addition of 0.21 g of N,N'-dicyclohexylcarbodiimide (DCC) and 0.02 g of 4-pyrrolidinopyridine under stirring at room temperature and further stirring for 6 hours at room temperature. After the reaction, the resultant N,N'-dicyclohexylurea was recovered by filtration, followed by washing with methylene chloride to be added to the filtrate. The solvent of the resultant filtrate was distilled-off under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene), followed by two times of recrystallization from a mixture solvent of toluene/methanol to obtain 0.39 g of 2-(p-hexylcarbonyloxyphenyl)-6-hexylbenzothiazole (Yield: 88.6%). ##STR203##

Workup

  1. stirringfurther stirring for 6 hours at room temperature
  2. customAfter the reaction
  3. filtrationthe resultant N,N'-dicyclohexylurea was recovered by filtration
  4. washby washing with methylene chloride
  5. additionto be added to the filtrate
  6. customto obtain a residue
  7. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  8. customfollowed by two times of recrystallization from a mixture solvent of toluene/methanol

Sources & evidence

ORD record
ord-97c8bfcb5323452c980376dcac07645c
Source dataset
uspto-grants-1993_08
Patent number
US05236619

Reaction notes

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