Phenyl isocyanate → HCID 44389607, compound

HRID 1176841Notes

Reaction equation

HRID 1176841 reaction equation
[SH:1][CH2:2][C:3](NCCCCCNC(NC1C=CC=CC=1)=O)=[O:4].[NH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28].[C:29]1([N:35]=[C:36]=[O:37])C=CC=CC=1.N([C:41]1[CH:46]=[CH:45][C:44]([N:47]([CH3:49])[CH3:48])=[CH:43][CH:42]=1)=C=O>>[CH3:49][N:47]([CH3:48])[C:44]1[CH:43]=[CH:42][C:41]([CH2:29][NH:35][C:36](=[O:37])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:3](=[O:4])[CH2:2][SH:1])=[CH:46][CH:45]=1

Participants

5

Reactant 4

HCID 7672Phenyl isocyanateHCID 16402HexamethylenediamineHCID 27333724-(Dimethylamino)phenyl isocyanateHCID 44389608N-{5-[(Phenylcarbamoyl)amino]pentyl}-2-sulfanylacetamide

Product 1

HCID 44389607HCID 44389607, compound

Procedure

Compound 12 was prepared using the methodology described for the preparation of compound 9, by substituting 1,5-diaminopentane with 1,6-diaminohexane and phenylisocyanate with (4-isocyanato-phenyl)-dimethyl-amine. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 7.98 (br s, 1H), 7.05 (d, J=8.7 Hz, 2H), 6.60 (d, J=8.7 Hz, 2H), 6.04 (br t, J=5.7 Hz, 1H), 5.80 (br t, J=5.7 Hz, 1H), 4.05 (d, J=5.7 Hz, 2H), 3.06 (d, J=8.1 Hz, 2H), 3.04 (dt, J=6.9, 6.0 Hz, 2H), 2.98 (dt, J=6.6, 6.0 Hz, 2H), 2.84 (s, 6H), 2.71 (t, J=8.1 Hz, 1H), 1.36 (m, 4H), 1.24 (m, 4H). 13C NMR (75 MHz, DMSO-d6) δ (ppm) 169.2, 157.9, 149.3, 127.9, 126.9, 112.3, 42.4, 40.3, 39.1, 38.7, 30.0, 29.0, 27.1, 26.12, 26.08.

Sources & evidence

ORD record
ord-6ce0215b899f4360989e386b0535f422
Source dataset
uspto-grants-2010_11
Patent number
US07842835B2

Reaction notes

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