Ethyl isocyanate → HCID 59603073, compound

HRID 2068709Notes

Reaction equation

HRID 2068709 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[CH:7][C:5]=2[N:6]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>O1CCOCC1>[CH2:13]([NH:15][C:16]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[CH:7][C:5]=2[N:6]=1)=[O:17])[CH3:14]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 59603069HCID 59603069, compound

Product 1

HCID 59603073HCID 59603073, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
62.5 °C

Procedure

To the solution of 2-amino-6-methyl-benzothiazol-5-ol (0.20 g, 1.11 mmol) in 1,4-dioxane (5 mL) was added ethylisocyanate (0.13 mL, 1.68 mmol) at room temperature. The resulting mixture was heated to 60-65° C. for 16 h. After completion of reaction (TLC monitoring), 1,4-dioxane was distilled off and co-evaporated with hexane (twice). The solid residue was treated with water to 60-70° C. for 2-4 h. The resulting solid was filtered off and dried under vacuum to obtain the white solid compound (0.17 g, 61%). 1H NMR (DMSO-d6, 400 MHz): δ 1.07 (t, J=7.20 Hz, 3H), 2.17 (s, 3H), 3.16 (m, 2H), 6.68 (br s, 1H), 7.00 (s, 1H), 7.47 (s, 1H), 9.33 (s, 1H), and 10.43 (br s, 1H), MS: 252.18 (M+H+).

Workup

  1. distillationwas distilled off
  2. additionThe solid residue was treated with water to 60-70° C. for 2-4 h
  3. filtrationThe resulting solid was filtered off
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c5c07d56cb16481e9c26c98db2a18dbf
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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