1,5-Diisocyanato-2-methylpentane → HCID 23296768, compound

HRID 1954315Notes

Reaction equation

HRID 1954315 reaction equation
[N:1]([CH2:4][CH:5]([CH3:12])[CH2:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11])=[C:2]=[O:3].[CH2:13]([CH:15]([NH:18][OH:19])[CH2:16][CH3:17])[CH3:14]>ClCCl>[CH3:12][CH:5]([CH2:6][CH2:7][CH2:8][NH:9][C:10]([N:18]([CH:15]([CH2:16][CH3:17])[CH2:13][CH3:14])[OH:19])=[O:11])[CH2:4][NH:1][C:2]([N:18]([OH:19])[CH:15]([CH2:16][CH3:17])[CH2:13][CH3:14])=[O:3]

Participants

4

Reactant 2

HCID 33434841,5-Diisocyanato-2-methylpentaneHCID 19073513N-(pentan-3-yl)hydroxylamine

Product 1

HCID 23296768HCID 23296768, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,5-Diisocyanato-2-methylpentane (3.2 ml, 20 mmol) was added dropwise to a solution of N-(1-ethylpropyl)hydroxylamine (4.4 g, 43 mmol) in dichloromethane (200 ml). The reaction was maintained overnight and then concentrated (in vacuo) to a volume of approximately 20 ml. Purification of the sample by flash column chromatography (96:4 dichloromethane.backslash.methanol, Rf 0.26) followed by recrystallization from N,N-dimethylformamide.backslash.water provided 2.6 g of the desired product as a white powder: MP: 124.0-125.0° C.; 1H NMR (300 MHz, DMSO): δ 8.70 (s, 1H), 8.66 (s, 1H), 6.73 (t, J=6.0 Hz, 1H), 6.68 (t, J=7.0 Hz, 1H), 3.81-3.72 (m, 2H), 3.02-2.78 (m, 4H), 1.60-0.98 (m, 13H), 0.83-0.77 (m, 15H); 13C NMR (75 MHz, DMSO): δ 160.95, 160.92, 59.9, 45.4, 39.6, 33.1, 31.2, 27.5, 24.5, 17.5, 11.1; IR (KBr): 3428, 3177, 2969, 2930, 2876, 1639, 1540, 1462, 1378, 1266, 1167, 1142, 1062, 1034, 929, 770 cm-1 ; MS (FAB): m/e 375.2957 (375.2971 calc'd for C18H39N4O4, M+H); Anal. calc'd for C18H38N4O4 : C, 57.73; H, 10.23; N, 14.96. Found: C, 57.90; H, 10.19; N, 14.93.

Workup

  1. temperatureThe reaction was maintained overnight
  2. concentrationconcentrated (in vacuo) to a volume of approximately 20 ml
  3. customPurification of the sample by flash column chromatography (96:4 dichloromethane.backslash.methanol, Rf 0.26)
  4. customfollowed by recrystallization from N,N-dimethylformamide

Sources & evidence

ORD record
ord-aa6a212870554dcaac8b516f3c1200b8
Source dataset
uspto-grants-2000_09
Patent number
US06121323

Reaction notes

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