Ethyl isocyanatoacetate → HCID 66615075, compound

HRID 2046047Notes

Reaction equation

HRID 2046047 reaction equation
[CH2:1]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(C1C=CC(N)=CC=1)CCCCCCC.[N:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:33]=[O:34].N(CCC(OCC)=O)=C=O>>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH:14][C:33](=[O:34])[NH:32][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 4

HCID 76283Ethyl isocyanatoacetateHCID 853464-OctylanilineHCID 2733373Ethyl 3-isocyanatopropanoateHCID 152539141-(4-Octylphenyl)methanamine

Product 1

HCID 66615075HCID 66615075, compoundYield 75%

Procedure

When the product of Example 6, Step C was substituted for 4-n-octylaniline and ethyl 2-isocyanatoacetate was substituted for ethyl 3-isocyanatopropionate in Example 11, Step A, the identical process afforded the title compound in 75% yield, as a colourless solid. 1H-NMR (CDCl3) 7.18 (d, 2H, J=8 Hz); 7.11 (d, 2H, J=8 Hz); 4.86 (m, 1H); 4.78 (m, 1H); 4.32 (d, 2H, J=5.6 Hz); 4.16 (q, 2H, J=7.1 Hz); 3.97 (d, 2H, J=5.3 Hz); 2.56 (t, 2H, J=8 Hz); 1.56 (m, 2H); 1.25 (m, 13H); 0.86 (t, 3H, J=6.9 Hz).

Sources & evidence

ORD record
ord-5ef2ba068fba4ea3be7899cd36bad177
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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