Ethyl isocyanate → HCID 59603111, compound

HRID 2068713Notes

Reaction equation

HRID 2068713 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH2:11])[S:8][C:5]2=[N:6][CH:7]=1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH:11][C:15]([NH:14][CH2:12][CH3:13])=[O:16])[S:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 446127746-Bromo[1,3]thiazolo[5,4-b]pyridin-2-amine

Product 1

HCID 59603111HCID 59603111, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromothiazolo[5,4-b]pyridin-2-amine IV (1.30 g, 5.55 mmol) in 1,4-dioxane (20.0 mL) was added ethylisocyanate (2.19 mL, 27.07 mmol) and the resulting reaction mixture was heated to 80° C. for 8 h. After the completion of the reaction (TLC monitoring), 1,4-dioxane was distilled off followed by co-distillation with n-hexane (2 times). The residue was then stirred with water at 90° C. for 2 h followed by filtration to obtain the desired product that was further washed with hot water and then dried. The residue was finally washed with ether to obtain the desired product (1.40 g, 83%). 1H NMR (400 MHz, DMSO-d6): δ 1.10 (t, J=7.20 Hz, 3H), 3.20 (quintet, J=7.20 Hz, 2H), 6.76 (br s, 1H), 8.24 (d, J=2.0 Hz, 1H), 8.45 (d, J=2.0 Hz, 1H) and 11.05 (br s, 1H).

Workup

  1. customthe resulting reaction mixture
  2. distillationwas distilled off
  3. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-bc83d38a71d24423a42a08fbac895e42
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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