Ethyl isocyanate → 1-Ethyl-3-(6-methoxy-1,3-benzothiazol-2-yl)urea

HRID 712180Notes

Reaction equation

HRID 712180 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([NH2:10])[S:9][C:5]=2[CH:4]=1.C(N(CC)CC)C.[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21]>CS(C)=O>[CH2:20]([NH:22][C:23]([NH:10][C:8]1[S:9][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=2[N:7]=1)=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 156302-Amino-6-methoxybenzothiazole

Product 1

HCID 168004671-Ethyl-3-(6-methoxy-1,3-benzothiazol-2-yl)urea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Methoxy-1,3-benzothiazol-2-amine (5.00 g, 27.74 mmol) was dissolved in anhydrous DMSO (20 mL) and triethylamine (15.50 mL, 110.97 mmol) followed by ethyl isocyanate (4.39 mL, 55.49 mmol). The mixture was stirred at rt under N2 for 4 h then quenched with water (˜200 mL) and stirred for 1 h. A white solid formed, was collected by filtration, rinsed with water then washed with acetone (100 mL) and the filtrate collected separately to the aqueous filtrate. The solid was partially soluble in acetone so the filtrate was concentrated to dryness under reduced pressure and combined with the solid collected by filtration to obtain the desired compound as a white solid, 6.27 g (90%). m/z: 251.96 [M+H]+.

Workup

  1. customthen quenched with water (˜200 mL)
  2. stirringstirred for 1 h
  3. customA white solid formed
  4. filtrationwas collected by filtration
  5. washrinsed with water
  6. washthen washed with acetone (100 mL)
  7. customthe filtrate collected separately to the aqueous filtrate
  8. concentrationwas concentrated to dryness under reduced pressure
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-307dcd8e1af84368808a594dc911e97a
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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