1,1'-Thiocarbonyldiimidazole → HCID 86675575, compound

HRID 2274155Notes

Reaction equation

HRID 2274155 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:24])[CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1.[C:25](N1C=CN=C1)([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)=[S:26]>O1CCCC1.CN(C)C1C=CN=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:24][C:25]([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)=[S:26])[CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:12]1

Participants

5

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 68243204HCID 68243204, compound

Product 1

HCID 86675575HCID 86675575, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (2.87 mmol) of tert-butyl 3-(benzothiazol-2-ylhydroxymethyl)piperidine-1-carboxylate were dissolved in 30 ml of tetrahydrofuran at room temperature. 0.35 g (2.87 mmol) of dimethylpyridin-4-ylamine and 1.53 g (8.61 mmol) of 1,1′-thiocarbonyldiimidazole were subsequently added. The reaction mixture was then stirred at room temperature for 18 h. Conventional work-up gave 1.08 g of tert-butyl 3-[benzothiazol-2-yl(imidazole-1-carbothioyloxy)methyl]piperidine-1-carboxylate; HPLC/MS (M+H)+=459 as oil.

Sources & evidence

ORD record
ord-da5a00ddcc8b4104b0edaae8da7ea712
Source dataset
uspto-grants-2015_09
Patent number
US09126952B2

Reaction notes

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