Water → N-Butylhydrazinecarboxylic acid phenyl ester

HRID 1744813Notes

Reaction equation

HRID 1744813 reaction equation
[CH2:1]([NH:5][NH2:6])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].O>ClCCl>[C:18]1([O:17][C:15]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[NH2:6])=[O:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 77064Butylhydrazine

Product 1

HCID 69640160N-Butylhydrazinecarboxylic acid phenyl esterYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of butylhydrazine (370 mg, 4.20 mmol) and triethylamine (0.88 mL, 6.30 mmol) in dichloromethane (15 mL) at 0° C. was added phenyl chloroformate (0.53 mL, 4.20 mmol). The reaction mixture was stirred and allowed to warm up to room temperature overnight. Water (20 mL) was then added to the reaction mixture. The aqueous layer was extracted with dichloromethane (20 mL×2). The combined organic layers were dried (MgSO4). Filtration and evaporation under vacuum, followed by purification by flash column chromatography provided the title compound (250 mg, 29%). 1H NMR (400 MHz, CHCl3) δ 7.40-7.10 (m, 5H), 4.20 (t, J=7.1 Hz, 2H), 3.60 (br s, 2H), 1.71 (m, 2H), 1.41 (m, 2H), 0.98 (t, J=7.3 Hz, 3H). MH+209.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (20 mL×2)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationFiltration and evaporation under vacuum
  4. customfollowed by purification by flash column chromatography

Sources & evidence

ORD record
ord-eab7ff3cbaa045b58fc539bdc938d0a4
Source dataset
uspto-grants-2006_03
Patent number
US07019003B2

Reaction notes

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