Ethyl isocyanate → 1-(5,7-Dibromo-6-methoxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

HRID 712191Notes

Reaction equation

HRID 712191 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([Br:12])[C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.C(N(CC)CC)C.[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>CS(C)=O.O>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([Br:12])[C:5]2[S:9][C:8]([NH:10][C:25]([NH:24][CH2:22][CH3:23])=[O:26])=[N:7][C:6]=2[CH:11]=1

Participants

6

Reactant 3

HCID 8022Ethyl isocyanate2×HCID 8471TriethylamineHCID 866639675,7-Dibromo-6-methoxy-1,3-benzothiazol-2-amine

Product 1

HCID 866639681-(5,7-Dibromo-6-methoxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

5,7-Dibromo-6-methoxy-1,3-benzothiazol-2-amine (208 mg, 0.62 mmol) was dissolved in anhydrous DMSO (1 mL) and triethylamine (0.189 mL, 1.35 mmol) followed by ethyl isocyanate (0.058 mL, 0.74 mmol). The mixture was stirred at rt. A further aliquot of ethyl isocyanate (0.058 mL, 0.74 mmol) was added after 3 h. After 3.75 h, the mixture was diluted with water and extracted into EtOAc (3×30 mL). The combined organic phases were washed with water and brine, dried over Na2SO4 and concentrated to dryness under reduced pressure. The desired compound was obtained as a pale yellow solid, 234 mg (93%). The material was used without further purification in the next step. m/z: 407.83/409.83/411.81 [M+H]+.

Workup

  1. extractionextracted into EtOAc (3×30 mL)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ae00cc4fc375451c9f709656272e723e
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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