1,1'-Thiocarbonyldiimidazole → HCID 178527811, compound

HRID 388601Notes

Reaction equation

HRID 388601 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[CH2:13]([NH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][C:22]=1[NH2:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.C1COCC1>[CH2:13]([N:20]1[C:21]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:31]=[C:1]1[SH:2])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 15224414HCID 15224414, compound

Product 1

HCID 178527811HCID 178527811, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Thiocarbonyldiimidazole (5.74 g, 32.2 mmol) was added to a solution of N4-benzylquinoline-3,4-diamine, see U.S. Pat. No. 4,689,338 (Gerster), Example 124, Parts A and B, (6.69 g, 26.8 mmol) in pyridine (50 mL) and THF (50 mL), and the reaction was heated at 80° C. for two hours and cooled to room temperature. A precipitate was present and was isolated by filtration and washed with diethyl ether to provide 4.17 g of 1-benzyl-1H-imidazo[4,5-c]quinoline-2-thiol as a white solid. The filtrate was treated with diethyl ether, and additional precipitate formed. The precipitate was isolated by filtration and washed with diethyl ether to provide an additional 1.90 g of product as a pale yellow solid.

Workup

  1. customwas isolated by filtration
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-e9ec973356d84538b348ac41ab1ca690
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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