1,1'-Thiocarbonyldiimidazole → HCID 86647857, compound

HRID 241205Notes

Reaction equation

HRID 241205 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[CH:23]=[C:24]([NH2:29])[C:25]([NH2:28])=[CH:26][CH:27]=4)[CH:20]=[CH:21][C:15]=3[O:14][CH2:13][CH2:12]2)=[CH:3][CH:2]=1.[C:30](N1C=CN=C1)(N1C=CN=C1)=[S:31]>O1CCCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]5[NH:28][C:30](=[S:31])[NH:29][C:24]=5[CH:23]=4)[CH:20]=[CH:21][C:15]=3[O:14][CH2:13][CH2:12]2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 66820332HCID 66820332, compound

Product 1

HCID 86647857HCID 86647857, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-quinolin-4-yl-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-benzene-1,2-diamine (630 mg, 1.65 mmol, synthesized according to the method of example 2 step) in tetrahydrofuran (30 mL) was added 1,1′-thiocarbonyldiimidazole (587 mg, 3.29 mmol), and the reaction mixture was stirred at room temperature for 20 h. The mixture was concentrated and the residue crystallized from methanol to give 5-(4-quinolin-4-yl-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-dihydro-2H-benzimidazole-2-thione (357 mg, 51% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6): 12.74 (s, 1H), 12.66 (s, 1H), 8.57 (d, 1H), 8.28 (d, 1H), 8.00 (d, 1H), 7.95 (m, 1H), 7.88 (d, 1H), 7.67 (m, 1H), 7.53 (dd, 1H), 7.49 (dd, 1H), 7.40 (s, 1H), 7.24 (d, 1H), 6.97 (m, 2H), 5.21 (s, 2H), 4.58 (m, 2H), 4.33 (m, 2H); MS (EI) for C25H20N4OS: 425 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue crystallized from methanol

Sources & evidence

ORD record
ord-590106f392c743cd8802566bf60e820a
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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