Methyl chloroformate → HCID 23326337, compound

HRID 1904049Notes

Reaction equation

HRID 1904049 reaction equation
[C:1]([OH:26])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[C:11][C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O.C([N:29]([CH2:32][CH3:33])CC)C.COC(Cl)=O.[CH3:39][CH:40]([NH2:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1>[CH3:39][CH:40]([NH:47][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]#[C:12][C:11]#[C:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([NH:29][CH:32]([CH3:33])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:26])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 74081-PhenethylamineHCID 8471TriethylamineHCID 54413810,12-Docosadiynedioic acid

Product 1

HCID 23326337HCID 23326337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 725 mg (2.00 mmol) of 10,12- docosadiyndioic acid in 50 ml THF was added 405 mg (4.00 mmol) of triethylamine. The solution was cooled to 0° C. and 378 mg (4.00 mmol) of methylchloroformate was added dropwise over one minute. The resulting white mixture was stirred one hour at 0° C., the 485 mg (4.00 mmol) of d(+, -α-methylbenzylamine was added. The reaction mixture was heated at reflux for one hour (gas evolution began immediately upon amine addition and ceased after 20 minutes). The mixture was cooled to room temperature and filtered. The filtrate was washed with 25 ml portions of 1 M HCl, water, and saturated aqueous sodium bicarbonate solution and dried (MgSO4). Evaporation yielded 842 mg (74% crude yield) of a white solid, which polymerized rapidly upon exposure to UV light. Recrystallization from ether-petroleum ether gave 456 mg of white crystals, m.p. 87.5°-89° C. I.R. (film): 1530, 1635, 2850, 2920, and 3300 cm-1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for one hour (gas evolution
  3. waitceased after 20 minutes
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered
  6. washThe filtrate was washed with 25 ml portions of 1 M HCl, water, and saturated aqueous sodium bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. customEvaporation
  9. customyielded 842 mg (74% crude yield) of a white solid, which
  10. custompolymerized rapidly upon exposure to UV light
  11. customRecrystallization from ether-petroleum ether

Sources & evidence

ORD record
ord-de491a7da93b46fa8138271c7ed3c7e4
Source dataset
uspto-grants-1984_03
Patent number
US04439514

Reaction notes

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