Tetrahydrofuran → HCID 13079429, compound

HRID 462473Notes

Reaction equation

HRID 462473 reaction equation
C(Cl)(=[O:3])N.[CH2:5]([NH:12][C:13](=[N:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[S:14][CH2:15][CH3:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>>[CH2:18]([N:17]([C:29]([O:28][CH2:27][C:26]#[CH:25])=[O:3])[C:13](=[N:12][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[S:14][CH2:15][CH3:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 20398502HCID 20398502, compound

Product 1

HCID 13079429HCID 13079429, compound

Conditions

Temperature
45 °C

Procedure

Then a solution of 15 ml dry THF and 5.44 g of the 1,3-diheptyl-2-ethyl isothiourea carbamyl chloride was added dropwise over 10 minutes. The mixture was stirred and warmed to 45° C. for 2 hours. The reaction was cooled to 25° C. and filtered by suction on a glass frit and filter. The solvent was removed under reduced pressure. 5.0 g of a liquid (88 weight percent of theory) having a nD30 of 1.4553 was recovered. The structure was confirmed as the title compound by NMR and spectra analyses. Compound No. 648 in Table I.

Workup

  1. temperatureThe reaction was cooled to 25° C.
  2. filtrationfiltered by suction on a glass frit
  3. filtrationfilter
  4. customThe solvent was removed under reduced pressure
  5. customwas recovered

Sources & evidence

ORD record
ord-f911d03bf1fb45d7a5e26469d2f250ca
Source dataset
uspto-grants-1985_05
Patent number
US04515813

Reaction notes

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