1,4-Diisocyanatobenzene → HCID 23296770, compound

HRID 1954314Notes

Reaction equation

HRID 1954314 reaction equation
[C:1]1([N:10]=[C:11]=[O:12])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[O:9])=[CH:3][CH:2]=1.[CH2:13]([CH:15]([NH:18][OH:19])[CH2:16][CH3:17])[CH3:14]>ClCCl>[C:1]1([NH:10][C:11]([N:18]([OH:19])[CH:15]([CH2:16][CH3:17])[CH2:13][CH3:14])=[O:12])[CH:2]=[CH:3][C:4]([NH:7][C:8]([N:18]([CH:15]([CH2:16][CH3:17])[CH2:13][CH3:14])[OH:19])=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 610091,4-DiisocyanatobenzeneHCID 19073513N-(pentan-3-yl)hydroxylamine

Product 1

HCID 23296770HCID 23296770, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same general procedure as reported in Example 13 was followed. 1,4-Phenylene diisocyanate (3.2 g, 20 mmol), N-(1-ethylpropyl)hydroxylamine (4.3 g, 42 mmol), and dichloromethane (200 ml) were combined. The product formed as a precipitate. Purification by recrystallization from N,N-dimethylformamide.backslash.water yielded 4.6 g of the desired product as a white powder: MP: 202.0° C. (decomp); 1H NMR (300 MHz, DMSO): δ 9.13 (s, 2H), 8.72 (s, 2H), 7.44 (s, 4H), 3.96-3.87 (septet, J=4.7 Hz, 2H), 1.60-1.33 (m, 8H), 0.84 (t, J=7.3 Hz, 12 H); 13C NMR (75 MHz, DMSO): δ 157.9, 134.0, 119.3, 59.6, 24.6, 11.1; IR (KBr): 3401, 3134, 2964, 2923, 2873, 1634, 1541, 1462, 1412, 1269, 1218, 1159, 1103, 1060, 833, 755, 736 cm-1 ; MS (FAB): m/e 367.2331 (367.2345 calc'd for C18H31N4O4, M+H); Anal. calc'd for C18H30N4O4 : C, 59.00; H, 8.25; N, 15.29. Found: C, 58.72; H, 8.34; N, 15.28.

Workup

  1. customThe product formed as a precipitate
  2. customPurification
  3. customby recrystallization from N,N-dimethylformamide

Sources & evidence

ORD record
ord-faaadeb55bb9406d868bb7d994afc77a
Source dataset
uspto-grants-2000_09
Patent number
US06121323

Reaction notes

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