Benzoyl chloride → HCID 13131616, compound

HRID 370454Notes

Reaction equation

HRID 370454 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S-:10][C:11]#[N:12].[NH4+].[NH2:14][N:15]1[CH2:23][C:22]2[C:17](=[C:18]([CH3:25])[CH:19]=[CH:20][C:21]=2[CH3:24])[CH2:16]1.[Cl-].[NH4+]>C(COC)OC>[C:1]([NH:12][C:11]([NH:14][N:15]1[CH2:16][C:17]2[C:22](=[C:21]([CH3:24])[CH:20]=[CH:19][C:18]=2[CH3:25])[CH2:23]1)=[S:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 25517Ammonium ChlorideHCID 13131604HCID 13131604, compound

Product 1

HCID 13131616HCID 13131616, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

4.4 g (0.031M) of benzoyl chloride in 10 ml of dimethoxyethane is dripped into a suspension of 2.5 g (0.033M) of ammonium thiocyanate in 50 ml of 1,2-dimethoxyethane. The mixture is stirred at room temperature for 1 hour. 4.5 g (0.028M) of 2-amino-4,7-dimethylisoindoline in 30 ml of dimethoxyethane are dripped in. The mixture is stirred at room temperature for 1 hour. The precipitated ammonium chloride is suctioned off. Evaporation yields 5.3 g of 1-benzoyl-3-(4,7-dimethylisoindolin-2-yl)-thiourea (Mp. 163°-164° C.) from the filtrate, which is converted by saponification with 50 ml of 10% sodium hydroxide into the (4,7-dimethylisoindolin-2-yl)-thiourea.

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour
  2. customEvaporation

Sources & evidence

ORD record
ord-2c6b5d933bdc43cb9412a3bc945ab7d4
Source dataset
uspto-grants-1985_07
Patent number
US04526897

Reaction notes

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