Triethylamine → N-(4-nitrophenoxycarbonyl)isopropoxylamine

HRID 1711150Notes

Reaction equation

HRID 1711150 reaction equation
[CH:1]([O:4][NH2:5])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:15]>C(Cl)Cl.[Cl-].[Na+].O>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][C:14]([NH:5][O:4][CH:1]([CH3:3])[CH3:2])=[O:15])=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 2768923Hydroxylamine, O-(1-methylethyl)-

Product 1

HCID 86629518N-(4-nitrophenoxycarbonyl)isopropoxylamineYield 56.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To as solution of the crude O-isopropyl-hydroxylamine (200 mg) from above in CH2Cl2 (5 ml) was added Et3N (0.30 ml, 2.16 mmol) and 4-nitrophenyl chloroformate (430 mg, 2.13 mmol) and the mixture stirred at room temperature for 30 min. before diluting with CH2Cl2 (20 ml) and brine (15 ml). The aqueous layer was extracted with CH2Cl2 (1×15 ml) and the combined organic extracts dried (Na2SO4), concentrated and purified by column chromatography on silica gel (Hexanes/EtOAc, 4:1) to afford N-(4-nitrophenoxycarbonyl)isopropoxylamine (290 mg) as a yellow oil.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (1×15 ml)
  2. dry with materialthe combined organic extracts dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (Hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-d5fd77cbc51d4a8fb605dec382356b4f
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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