Phosgene → 3-(6-Methoxy-m-tolyl)-1,2-benzisothiazol-5-yl isocyanate

HRID 1274546Notes

Reaction equation

HRID 1274546 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]3[CH:11]=[C:12]([CH3:18])[C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[C:6]=2[CH:19]=1.[C:20](Cl)(Cl)=[O:21]>C1(C)C=CC=CC=1>[CH3:17][O:16][C:13]1[C:12]([CH3:18])=[CH:11][C:10]([C:7]2[C:6]3[CH:19]=[C:2]([N:1]=[C:20]=[O:21])[CH:3]=[CH:4][C:5]=3[S:9][N:8]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 698320455-Amino-3-(6-methoxy-m-tolyl)-1,2-benzisothiazole

Product 1

HCID 867560853-(6-Methoxy-m-tolyl)-1,2-benzisothiazol-5-yl isocyanateYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 5-amino-3-(6-methoxy-m-tolyl)-1,2-benzisothiazole (157 g, 0.581 mol) in toluene is treated with phosgene (1,074 mL of a 20% solution in toluene, 2.06 mol), heated to and stirred at reflux for 5 hours, treated with additional phosgene (100 mL of a 20% solution in toluene), refluxed overnight, and concentrated in-vacuo to give the title product as a yellow-orange solid (169 g, 98.2%) which is identified by NMR spectral analyses.

Workup

  1. temperatureheated to and
  2. temperatureat reflux for 5 hours
  3. temperaturerefluxed overnight
  4. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-d993b934a3dc4eba81cba0b635054a69
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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