Hexane → HCID 86737052, compound

HRID 1706589Notes

Reaction equation

[CH2:1]([OH:8])[C:2]#[C:3][C:4]#[C:5][CH2:6][OH:7].C(N(CC)CC)C.[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[C:18]([N:22]=[C:23]=[O:24])[CH:17]=1.CCCCCC>C1COCC1>[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([O:7][CH2:6][CH3:5])=[O:24])[CH:17]=1.[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([O:7][CH2:6][CH3:5])=[O:24])[CH:17]=1.[CH2:1]([OH:8])[C:2]#[C:3][C:4]#[C:5][CH2:6][OH:7]

Participants

Conditions

Temperature: 25 °C

Procedure

A 500 ml 3-necked round bottom flask was fitted with a magnetic stirrer, an addition funnel and a thermometer. To the flask was added 11.0 grams (0.1 mole) of 2,4-hexadiyn-1,6-diol in 300 ml of THF, 0.5 g of di-t-butyltin-di-2-ethoxyhexanoate and 2 ml. of triethylamine. The resultant solution was stirred and 39.9 g (0.3 mole) of m-tolyl isocyanate was added dropwise over a period of half an hour. The reaction temperature was maintained at about 25° C. by a cold water bath. The reaction was allowed to proceed for 2 hours. Into the resultant solution about 1500 ml of hexane was poured. The precipitate was collected and dried under vacuum. The yield of the crude material was quantitative. Elemental and infrared analysis was conducted on a sample recrystallized from acetone-hexane, which was in the inactive form. The m.p. was 133° C. Analytical: Calculated for C,H,N,O: 70.21; 5.32; 7.45; 17.02. Found for C,H,N,O: 70.17; 5.20; 7.12; 17.21. Infrared spectrum (KBr Pellet):

Workup

customA 500 ml 3-necked round bottom flask was fitted with a magnetic stirrer, an addition funnel
customThe precipitate was collected
customdried under vacuum
customrecrystallized from acetone-hexane, which

Sources & evidence

ORD record: ord-c22ec23da3db4f89ab6e2235f962715b
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04208186

Reaction notes

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