Octadecyl isocyanate → HCID 19594339, compound

HRID 1440444Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[CH2:12]([N:30]=[C:31]=[O:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(C(C)=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH2:10][NH:11][C:31]([NH:30][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:32])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Into a 200-ml flask equipped with a stirrer and a condenser were charged 10.0 g of 2-(p-hydroxyphenylthio)ethylamine and 120 ml of methyl ethyl ketone, and stirred with heating at 60° C. in a nitrogen stream. Into the resulting solution was slowly dropped 15.3 g of n-octadecyl isocyanate, upon which white crystals were immediately precipiated. The reaction temperature was raised to 90° C. and stirring was continued with heating for 1 hour. The reaction mixture was cooled to room temperature, after which the crystals precipitated were collected by filtration. Recrystallization from chloroform gave 27.5 g of the desired compound. Melting point: 121° C.

Workup

customInto a 200-ml flask equipped with a stirrer and a condenser
temperatureThe reaction temperature was raised to 90° C.
stirringstirring
temperaturewith heating for 1 hour
temperatureThe reaction mixture was cooled to room temperature
customafter which the crystals precipitated
filtrationwere collected by filtration
customRecrystallization from chloroform

Sources & evidence

ORD record: ord-fa0b9abc85674237b94b9b753d6b63d9
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05498772

Reaction notes

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