O,O-Dipyridin-2-yl carbonothioate → HCID 15744956, compound

HRID 327464

Reaction equation

HRID 327464 reaction equation
N1C=CC=CC=1O[C:8](=[S:16])OC1C=CC=CN=1.[CH2:17]([N:20]([CH2:32][CH2:33][CH3:34])[CH:21]1[CH2:30][C:29]2[C:24](=[C:25]([NH2:31])[CH:26]=[CH:27][CH:28]=2)[NH:23][CH2:22]1)[CH2:18][CH3:19]>C1COCC1>[CH2:32]([N:20]([CH2:17][CH2:18][CH3:19])[CH:21]1[CH2:30][C:29]2[C:24]3=[C:25]([NH:31][C:8](=[S:16])[N:23]3[CH2:22]1)[CH:26]=[CH:27][CH:28]=2)[CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 15291950HCID 15291950, compound

Product 1

HCID 15744956HCID 15744956, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di (2-pyridyl)thiocarbonate (1.6 g, 7.2 mmol) was added to a stirred solution of 1,2,3,4-tetrahydro-N3,N3 -dipropyl-3,8-quinolinediamine (1.6 g, 6.7 mmol) in THF (50 mL). The solution was stirred for 1 hour, evaporated, and partitioned between chloroform and water. The chloroform phase was evaporated and chromatographed on silica gel using ethyl acetate:hexane (1:9) as the initial eluant to give 1.6 g of product. Crystallization from cyclohexane gave 1.3 g (67% of 5-(dipropylamino)-5,6-hydro-4H-imidazo(4,5,1-ij)quinolin-2(1H)-thione, mp 150°-151° C. Anal. Calcd. for C16H23N3S: C, 66.39; H, 8.01; N, 14.52; S, 11.08. Found: C, 66.50; H, 8.18; N, 14.56; S, 11.02.

Workup

  1. customevaporated
  2. custompartitioned between chloroform and water
  3. customThe chloroform phase was evaporated
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-1fa1d205a8424e799bafd9395f2f8439
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Linked notes

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