Thiophosgene → N,N"-Bis[2-((4-methoxybenzyl)thio)-2-methyl-propionyl]-N'-(4-isothiocyanatobenzyl)-diethylenetriamine

HRID 1781220Notes

Reaction equation

HRID 1781220 reaction equation
[CH3:1][O:2][C:3]1[CH:45]=[CH:44][C:6]([CH2:7][S:8][C:9]([CH3:43])([CH3:42])[C:10]([NH:12][CH2:13][CH2:14][N:15]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)[CH2:16][CH2:17][NH:18][C:19](=[O:33])[C:20]([CH3:32])([S:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH3:21])=[O:11])=[CH:5][CH:4]=1.[C:46](Cl)(Cl)=[S:47]>ClCCl>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][S:22][C:20]([CH3:32])([CH3:21])[C:19]([NH:18][CH2:17][CH2:16][N:15]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N:41]=[C:46]=[S:47])=[CH:37][CH:36]=2)[CH2:14][CH2:13][NH:12][C:10](=[O:11])[C:9]([CH3:43])([S:8][CH2:7][C:6]2[CH:44]=[CH:45][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:42])=[O:33])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 69828238N,N"-Bis[2-((4-methoxybenzyl)thio)-2-methyl-propionyl]-N'-(4-aminobenzyl)-diethylenetriamine

Product 1

HCID 86750868N,N"-Bis[2-((4-methoxybenzyl)thio)-2-methyl-propionyl]-N'-(4-isothiocyanatobenzyl)-diethylenetriamineYield 117.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a round bottom flask with the aniline 20 (55.7 mg, 0.0853 mmol) and dichloromethane (5 mL) was added 0.2011M solution of thiophosgene (0.42 mL, 0.0845 mmol) in dichloromethane. The heterogeneous reaction mixture was stirred at room temperature for 1 hour and the solvent was removed in vacuo to give the isothiocyanate 21 as a brown solid (68.9 mg, 116%).

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-091fa4e5f2d948a59c39c08379c63ae5
Source dataset
uspto-grants-1997_05
Patent number
US05632969

Reaction notes

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