Ammonium Hydroxide → HCID 178512504, compound

HRID 2212106Notes

Reaction equation

HRID 2212106 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[NH:13])SC)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH4+:14].[OH-]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:13])=[NH:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 178504002HCID 178504002, compound

Product 1

HCID 178512504HCID 178512504, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 13 (2.29 g, 6.31 mmol) in 23 ml of ethanol was added 6.87 ml of NH4OH. The reaction mixture was stirred at room temperature for 10 minutes, and the clear solution was refluxed for 12 hours. The solvent was removed under reduced pressure and the residue was suspended in saturated Na2CO3 solution. The solid was collected, washed sequentially with H2O and Et2O and dried to give the title compound as a white solid (1.16 g, 90%), mp 208° C. 1H NMR (600 MHz, DMSO-d6): δ 7.39 (d, J=8.6 Hz, 1H), 7.02 (d, J=2.4 Hz, 1H), 6.79 (dd, J=8.6 and 2.4 Hz, 1H), 5.79 (br s, 3H); 13C NMR: δ 155.38, 130.69, 130.28, 124.30, 123.50. IR: 1684, 1624, 1559, 1472, 1380, 1328, 869, 818, 671 cm−1. MS (m/z): 204 (M+), 187, 162, 127, and 90.

Workup

  1. temperaturethe clear solution was refluxed for 12 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe solid was collected
  4. washwashed sequentially with H2O and Et2O
  5. customdried

Sources & evidence

ORD record
ord-9f666f8073fe4442ac842d5e11b4f8ed
Source dataset
uspto-grants-2006_09
Patent number
US07101902B2

Reaction notes

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