Diethyl Ether → 1-(7-Bromo-5-iodobenzo[d]thiazol-2-yl)-3-ethylurea

HRID 712159Notes

Reaction equation

HRID 712159 reaction equation
[Br:1][C:2]1[C:10]2[S:9][C:8]([NH2:11])=[N:7][C:6]=2[CH:5]=[C:4]([I:12])[CH:3]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14].CCOCC.CCCCC>O1CCOCC1>[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C:16]([NH:15][CH2:13][CH3:14])=[O:17])=[N:7][C:6]=2[CH:5]=[C:4]([I:12])[CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8003PentaneHCID 8022Ethyl isocyanateHCID 578137597-Bromo-5-iodobenzothiazol-2-amine

Product 1

HCID 578137231-(7-Bromo-5-iodobenzo[d]thiazol-2-yl)-3-ethylureaYield 88.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 7-bromo-5-iodobenzothiazol-2-amine (250 g, 0.70 mol) in 1,4-dioxane at rt was added ethylisocyanate (278 mL, 3.52 mol). The resulting reaction mixture was heated to 80° C. for 10-12 h under N2 atmosphere. After reaction completion (by TLC), the solvent was evaporated then n-hexane added and the evaporation procedure repeated. The resulting residue was stirred in hot water (2 L) at 60-65° C. for 30-40 min then filtered. The residue thus obtained was treated with a mixture of Et2O and n-pentane and filtered to obtain the desired product (264 g, 88%). 1H NMR (DMSO-d6): δ 1.08 (t, J=7.20 Hz, 3H), 3.20 (q, J=6.80, 2H), 6.73 (br s, 1H), 7.72 (s, 1H), 7.96 (s, 1H) and 11.07 (br s, 1H). MS: 426.0 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customAfter reaction completion (by TLC)
  3. customthe solvent was evaporated
  4. additionn-hexane added
  5. customthe evaporation procedure
  6. filtrationthen filtered
  7. customThe residue thus obtained
  8. filtrationfiltered

Sources & evidence

ORD record
ord-ffe3dfbff43e4fe89e1abc3ba2a8f755
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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