Ethyl isocyanate → 1-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-urea

HRID 447057Notes

Reaction equation

HRID 447057 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Br:19])[C:12]2[S:16][C:15]([NH2:17])=[N:14][C:13]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Br:19])[C:12]2[S:16][C:15]([NH:17][C:23]([NH:22][CH2:20][CH3:21])=[O:24])=[N:14][C:13]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 578135885-(Benzyloxy)-7-bromobenzo[d]thiazol-2-amine

Product 1

HCID 578136291-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-ureaYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-benzyloxy-7-bromo-benzothiazol-2-ylamine (1.35 g, 4.02 mmol) in dioxane (50.0 mL) was added ethyl isocyanate (1.90 mL, 24.22 mmol) and the resulting reaction mixture was heated to 80° C. for 15 h. The solvent was then evaporated and the residue was stirred in water at 85° C. for 5-6 h. The solution was then filtered and the solid thus obtained was washed with hot water and hexane to get the desired product (1.50 g, 92%) as an off-white solid. M.P. 294.2° C.

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was then evaporated
  3. filtrationThe solution was then filtered
  4. customthe solid thus obtained
  5. washwas washed with hot water and hexane

Sources & evidence

ORD record
ord-f7aee6b52a834f628b18432c36fbfdc8
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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