Ammonia → HCID 89807072, compound

HRID 1399987Notes

Reaction equation

HRID 1399987 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][O:12]1)[NH2:5].[S-:16][C:17]#[N:18].[NH4+].BrBr.N>C(O)(=O)C>[Br:1][C:2]1[C:8]([O:9][CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)=[CH:7][C:6]2[S:16][C:17]([NH2:18])=[N:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 15666Ammonium thiocyanateHCID 24408BromineHCID 61720985HCID 61720985, compound

Product 1

HCID 89807072HCID 89807072, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of ii (3.0 g, 11.62 mmol) in acetic acid (50 mL) was added ammonium thiocynate (4.18 g, 55.11 mmol) at RT. The resulting mixture was stirred at RT for 15 min followed by the addition of bromine (0.68 mL, 13.22 mmol) in acetic acid (5 mL). The mixture was stirred at RT for 5 h. The pH was adjusted to >7 with ammonia solution followed by extraction with EtOAc (2×200 mL). The combined organics were washed with H2O, brine solution, dried (Na2SO4) and concentrated in vacuo. The residue was purified over silica (60% EtOAc-Hexanes) to obtain iii (1.0 g, 26%). 1HNMR (DMSO-d6, 400 MHz): δ 7.50 (s, 1H), 7.49 (s, 1H), 7.43 (br s, 2H), 4.18 (m, 1H), 3.96 (m, 2H), 3.80 (m, 1H), 3.69 (m, 1H), 1.96 (m, 2H) and 1.78 (m, 2H). MS: 329.0 [M+H]+.

Workup

  1. stirringThe mixture was stirred at RT for 5 h
  2. extractionfollowed by extraction with EtOAc (2×200 mL)
  3. washThe combined organics were washed with H2O, brine solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified over silica (60% EtOAc-Hexanes)

Sources & evidence

ORD record
ord-bcbf566154c14df6844897a1c392510f
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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