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

HRID 1941978Notes

Reaction equation

HRID 1941978 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-d14d3576c7f5451baee2fee9e2eaa190
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

Loading…