Butyl bromide → HCID 18917708, compound

HRID 2077269Notes

Reaction equation

HRID 2077269 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Br[CH2:20][CH2:21][CH2:22][CH3:23]>C(#N)C>[C:1]([O:5][C:6]([NH:7][NH:8][CH2:20][CH2:21][CH2:22][CH3:23])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 70091tert-Butyl carbazateHCID 81531Diisopropylethylamine

Product 1

HCID 18917708HCID 18917708, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a magnetically stirred solution of tert-butylcarbazate (47.5 gram, 359 mmol) in anhydrous acetonitrile (300 ml) was successively added DIPEA (Hünig's base) (37.6 ml, 216 mmol) and 1-bromobutane (19.3 ml, 180 mmol). The resulting mixture was reacted at 60° C. for 16 hours. The resulting mixture was allowed to attain room temperature and subsequently concentrated in vacuo and further purified by Sepacore chromatography (eluant: petroleum ether 40-60/ethylacetate=4/1 (v/v)) to give N′-butylhydrazine-carboxylic acid tert-butyl ester (intermediate XIII-1) (13.2 gram, 39%) as a pale yellow oil: 1H-NMR (400 MHz, CDCl3) δ 0.91 (t, J=7, 3H), 1.30-1.49 (m, 13H), 2.81-2.87 (m, 2H), 4.00 (br s, 1H), 6.20 (br s, 1H).

Workup

  1. customThe resulting mixture was reacted at 60° C. for 16 hours
  2. customto attain room temperature
  3. concentrationsubsequently concentrated in vacuo
  4. customfurther purified by Sepacore chromatography (eluant: petroleum ether 40-60/ethylacetate=4/1 (v/v))

Sources & evidence

ORD record
ord-2f3ff2e5d2104de5a1ba9f8d512e1ace
Source dataset
uspto-grants-2011_04
Patent number
US07928134B2

Reaction notes

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