Ethyl isocyanate → HCID 86696900, compound

HRID 1399988Notes

Reaction equation

HRID 1399988 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][O:15]2)=[CH:4][C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20]>O1CCOCC1>[Br:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][O:15]2)=[CH:4][C:5]2[S:9][C:8]([NH:10][C:22]([NH:21][CH2:19][CH3:20])=[O:23])=[N:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 89807072HCID 89807072, compound

Product 1

HCID 86696900HCID 86696900, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of iii (1.0 g, 3.03 mmol) in 1,4-dioxane (10 mL) was added ethyl isocynate (1.23 mL, 15.19 mmol) at RT. The mixture was stirred at 80° C. for 5 h. The reaction mixture was evaporated in vacuo, H2O (50 mL) added to and the mixture stirred at 70° C. for 4 h. The residue was filtered and dried under vacuum to obtain iv (1.0 g, 83%). 1HNMR (DMSO-d6, 400 MHz): δ 10.69 (br s, 1H), 7.80 (s, 1H), 7.68 (s, 1H), 6.65 (m, 1H), 4.21 (m, 1H), 4.04 (m, 2H), 3.83 (m, 1H), 3.70 (m, 1H), 3.16 (m, 2H), 2.0 (m, 2H), 1.82 (m, 2H) and 1.09 (t, J=7.20 Hz, 3H). MS: 400 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated in vacuo, H2O (50 mL)
  2. additionadded to and the mixture
  3. stirringstirred at 70° C. for 4 h
  4. filtrationThe residue was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-bf9220b582ac4d089c4c188f54604fd9
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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