Diphenylmethane diisocyanate → HCID 9804100, compound

HRID 1954312Notes

Reaction equation

HRID 1954312 reaction equation
[CH:1]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]=[C:15]=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=[C:3]([N:17]=[C:18]=[O:19])[CH:2]=1.[CH2:20]([CH:22]([NH:25][OH:26])[CH2:23][CH3:24])[CH3:21]>O1CCCC1>[CH2:7]([C:6]1[CH:5]=[CH:4][C:3]([NH:17][C:18](=[O:19])[N:25]([OH:26])[CH:22]([CH2:23][CH3:24])[CH2:20][CH3:21])=[CH:2][CH:1]=1)[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:16])[N:25]([CH:22]([CH2:23][CH3:24])[CH2:20][CH3:21])[OH:26])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7570Diphenylmethane diisocyanateHCID 19073513N-(pentan-3-yl)hydroxylamine

Product 1

HCID 9804100HCID 9804100, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,4'-methylenebis(phenylisocyanate) (1.5 g, 6.0 mmol) and tetrahydrofuran (75 ml) was charged with N-(1-ethylpropyl)hydroxylamine (1.5 g, 14.5 mmol) and maintained at ambient temperature for 16 hr. The solvent was removed in vacuo to provide the crude product as a white solid. Recrystallization from ethyl acetate.backslash.hexanes provided 1.0 g of the desired product as a white powder: MP: 196.0-198.0° C. (decomp); 1H NMR (300 MHz, DMSO): δ 9.16 (s, 2H), 8.78 (s, 2H), 7.50 (d, J=8.5 Hz, 4H), 7.05 (d, J=8.5 Hz, 4H), 3.96-3.87 (m 2H), 3.77 (s, 2H), 1.59-1.31 (m, 8H), 0.85-0.80 (t, J=7.3 Hz, 12H); 13C NMR (75 MHz, DMSO): δ 157.7, 137.4, 134.9, 128.2, 119.1, 59.6, 24.5, 11.0; IR (KBr): 3395, 3147, 2966, 2931, 2875, 1641, 1590, 1528, 1461, 1413, 1328, 1312, 1225, 1150, 815, 761 cm-1 ; MS (FAB): m/e 457.2804 (457.2815 calc'd for C25H37N4O4, M+H); Anal. calc'd for C25H36N4O4 : C, 65.76; H, 7.95; N, 12.27. Found: C, 65.53; H, 7.87; N, 12.11.

Workup

  1. customThe solvent was removed in vacuo
  2. customto provide the crude product as a white solid
  3. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-72a0a5735ca64d44840fa21d58f9c116
Source dataset
uspto-grants-2000_09
Patent number
US06121323

Reaction notes

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