Octadecyl isocyanate → C18H37Nhcosch2CH2C8F17

HRID 1441130Notes

Reaction equation

[CH2:1]([N:19]=[C:20]=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:22]([CH2:47][CH2:48][SH:49])([C:25]([C:28]([C:31]([C:34]([C:37]([C:40]([C:43]([F:46])([F:45])[F:44])([F:42])[F:41])([F:39])[F:38])([F:36])[F:35])([F:33])[F:32])([F:30])[F:29])([F:27])[F:26])([F:24])[F:23].N1(C2CCCCCCC2)CCCCCCN1>>[CH2:1]([NH:19][C:20]([S:49][CH2:48][CH2:47][C:22]([C:25]([C:28]([C:31]([C:34]([C:37]([C:40]([C:43]([F:44])([F:45])[F:46])([F:41])[F:42])([F:38])[F:39])([F:35])[F:36])([F:33])[F:32])([F:30])[F:29])([F:27])[F:26])([F:24])[F:23])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Reactant 3

HCID 66988Octadecyl isocyanate

HCID 5427551,1,2,2-Tetrahydroperfluorodecanethiol

HCID 66583054Diazabicyclooctane

Product 1

HCID 131719351C18H37Nhcosch2CH2C8F17

Conditions

Temperature: 100 °C

Procedure

Octadecyl Isocyanate (29.5 g, 0.1 mole), C8F17CH2CH2SH (48 g, 0.1 moles) and 2.2.2 diazabicyclooctane (0.1 g) were mixed under nitrogen and heated to 100° C. with stirring for 6 hours. An infrared spectrum showed no -NCO absorption, indicating completion of the reaction. The product is a white wax, melting at 85°-89° C. NMR showed proton resonances at 4.7 ppm (1 proton NH), 3.2 ppm (2 protons CH2CH2NH), 3.1 ppm (2 protons CH2SCO), 2.5 ppm (2 protons C8F17CH2), 1.3 ppm (32 protons CH3 (CH2)16) and 0.8 ppm (3 protons CH3 (CH2)16).

Workup

customno -NCO absorption
customcompletion of the reaction

Sources & evidence

ORD record: ord-7ba3476d200c49568ad15e86cc97937f
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05502225

Reaction notes

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