1,1'-Thiocarbonyldiimidazole → HCID 86594693, compound

HRID 491692Notes

Reaction equation

HRID 491692 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH3:15])[CH3:14])[CH2:9]1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[S:19]>C(Cl)Cl>[Cl:17][C:5]1[CH:4]=[CH:3][C:2]([N:1]=[C:18]=[S:19])=[CH:16][C:6]=1[CH2:7][N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH3:14])[CH3:15])[CH2:9]1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 63166005HCID 63166005, compound

Product 1

HCID 86594693HCID 86594693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(5-Amino-2-chloro-benzyl)-pyrrolidin-3-yl]-dimethyl-amine (Step f, 1.2 g, 4.7 mmol, 1.0 eq.) was dissolved into CH2Cl2 (100 ml) and 1,1′-thiocarbonyldiimidazole (0.85 g, 4.7 mmol, 1.0 eq.) was added. The reaction was stirred at RT for 2 h. TLC showed conversion of starting material into product. Concentrated down to dryness and purified by column chromatography (100% EtOAc) to give [1-(2-chloro-5-isothiocyanato-benzyl)-pyrrolidin-3-yl]-dimethyl-amine.

Workup

  1. additionwas added
  2. concentrationConcentrated down to dryness
  3. custompurified by column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-7b1aab1c42354253a70467acc9f623eb
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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