Hydrochloric Acid → HCID 69300805, compound

HRID 131285Notes

Reaction equation

HRID 131285 reaction equation
[CH2:1]([NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].C(N(CC)C(C)C)(C)C.Cl>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([N:8]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=1)[C:24](=[O:25])[CH2:23][CH2:22][CH2:21][Cl:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 783704-Chlorobutyryl chlorideHCID 81531DiisopropylethylamineHCID 3832836Ethyl 4-(benzylamino)benzoate

Product 1

HCID 69300805HCID 69300805, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-benzylaminobenzoate (6.0 g) in methylene chloride (60 mL) is added dropwise chlorobutyryl chloride (3.95 mL) and N,N-diisopropylethylamine (6.14 mL) under ice-cooling, and the mixture is stirred for 12 hours. The reaction mixture is diluted with chloroform and thereto is added 10% HCl. The organic layer is separated, washed successively with water, a saturated sodium hydrogencarbonate solution, water, and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by flash column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=4:1) to give ethyl 4-[N-benzyl-N-(4-chlorobutyryl)amino]benzoate (8.27 g, yield; quantitative) as an oil. MS (APCI) m/z; 360/362 [M+H]+

Workup

  1. temperaturecooling
  2. customThe organic layer is separated
  3. washwashed successively with water
  4. dry with materiala saturated sodium hydrogencarbonate solution, water, and saturated brine, dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-3a129cab96f347c082e7fba86edc7c97
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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