Butyl isocyanate → HCID 69299765, compound

HRID 131265Notes

Reaction equation

HRID 131265 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1.[CH2:18]([N:22]=[C:23]=[O:24])[CH2:19][CH2:20][CH3:21].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:18]([NH:22][C:23]([N:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=1)[CH2:4][CH2:3][N:2]([CH3:1])[CH3:17])=[O:24])[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8110Butyl isocyanateHCID 516892Sodium BicarbonateHCID 16781125HCID 16781125, compound

Product 1

HCID 69299765HCID 69299765, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-[[[2-(dimethylamino)ethyl]amino]methyl]benzoate (compound obtained in Reference Example 36(1), 200 mg) in methylene chloride (4 mL) is added n-butyl isocyanate (143 μL) and the mixture is stirred at room temperature for 4 hours. The reaction mixture is diluted with chloroform (5 mL) and thereto is added a saturated sodium hydrogencarbonate solution (10 mL). After stirring, the organic layer is separated and concentrated. The resultant crude product is purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10) to give methyl 4-[[N-(butylcarbamoyl)-N-[2-(dimethylamino)ethyl]amino]methyl]-benzoate (261 mg, yield; 92%) as a pale yellow oil. MS (APCI) m/z: 336 [M+H]+

Workup

  1. stirringAfter stirring
  2. customthe organic layer is separated
  3. concentrationconcentrated
  4. customThe resultant crude product is purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10)

Sources & evidence

ORD record
ord-f89f7e102876489ca8f944a4d3c36205
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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