1-Hydroxybenzotriazole → HCID 22467378, compound

HRID 1934659Notes

Reaction equation

HRID 1934659 reaction equation
[CH:1]1([NH:6][C:7]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=2[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[O:41]1[C:45]2[CH:46]=[CH:47][C:48]([CH2:50][NH2:51])=[CH:49][C:44]=2[O:43][CH2:42]1>CN(C)C=O>[CH:1]1([NH:6][C:7]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=2[C:9]([NH:51][CH2:50][C:48]2[CH:47]=[CH:46][C:45]3[O:41][CH2:42][O:43][C:44]=3[CH:49]=2)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11470697HCID 11470697, compound

Product 1

HCID 22467378HCID 22467378, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-cyclopentylamino-5-nitrobenzoic acid (1.00 g), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.15 g), 1-hydroxybenzotriazole (810 mg) in anhydrous dimethylformamide (10 mL) was added (1,3-benzodioxol-5-ylmethyl)amine (725 mg), and the mixture was stirred for 15 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with an aqueous saturated sodium bicarbonate solution, water and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of chloroform and methanol (50:1). The obtained product was triturated with diisopropyl ether and recrystallized from a mixture of hexane and ethyl acetate to give 2-cyclopentylamino-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (1.51 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with an aqueous saturated sodium bicarbonate solution, water and brine
  4. dry with materialThen, the resultant was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by a silica gel column chromatography
  7. washeluting with a mixture of chloroform and methanol (50:1)
  8. customThe obtained product was triturated with diisopropyl ether
  9. customrecrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-9d93cc97e807408fa90d81e7f7728f6c
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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