Dimethylthiocarbamoyl chloride → HCID 59305855, compound

HRID 2240920Notes

Reaction equation

HRID 2240920 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH:5]2[CH2:8][CH2:9][CH2:10][CH2:11][CH:4]2[C:3]1=[O:12].[CH3:13][N:14]([CH3:18])[C:15](Cl)=[S:16]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:7]=[C:6]1[CH:5]2[CH:4]([CH2:11][CH2:10][CH2:9][CH2:8]2)[C:3](=[O:12])[N:2]1[O:1][C:15](=[S:16])[N:14]([CH3:18])[CH3:13]

Participants

5

Reactant 2

HCID 27871Dimethylthiocarbamoyl chlorideHCID 2249812-hydroxyhexahydro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59305855HCID 59305855, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 25.38 g (0.15 mol) of N-hydroxy-hexahydrophthalimide (prepared as described in Chem. Pharm. Bull., 16, (1968), 622) and 0.5 g 4-dimethylaminopyridine in 100 ml pyridine were added 18.54 g (0.15 mol) of dimethylthiocarbamoyl chloride. The mixture was stirred at room temperature during 3 h and then poured into 1000 ml of ice water. The precipitate was filtered off and recrystallized from 120 ml of ethanol to give 28.38 g of white crystals, mp. 124-126° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. customrecrystallized from 120 ml of ethanol

Sources & evidence

ORD record
ord-805957550dba44a2ba359496481555b1
Source dataset
uspto-grants-2010_05
Patent number
US07723399B2

Reaction notes

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