Ammonia → HCID 10340604, compound

HRID 1085138Notes

Reaction equation

HRID 1085138 reaction equation
[CH3:1][C:2]1[C:29]([CH3:30])=[CH:28][C:5]2[NH:6][C:7](=S)[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1.[NH3:31]>C(O)CCC.CO>[NH2:31][C:7]1[CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:25]4[CH:24]=[CH:23][N:22]=[CH:21][C:20]=4[N:19]=[C:18]3[CH3:26])=[CH:13][CH:12]=2)=[N:10][C:4]2[CH:3]=[C:2]([CH3:1])[C:29]([CH3:30])=[CH:28][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 10024618HCID 10024618, compound

Product 1

HCID 10340604HCID 10340604, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of the thioamide (from Example 19) (2.98 g, 7.24 mmol) and red mercuric oxide (1.57 g, 7.24 mmol) in n-butanol (40 ml) was saturated with ammonia gas at room temperature, and then stirred at 120° C. for 3 hours. After being cooled, the mixture was diluted with methanol (150 ml) and filtered through Arbocel filter aid. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (eluting with ethyl acetate:methanol:diethylamine=100:10:5). Fractions containing the product were evaporated to give the title compound as a bright yellow solid (1.085 g, 38%), m.p. 299°-302° C.

Workup

  1. temperatureAfter being cooled
  2. filtrationfiltered through Arbocel
  3. filtrationfilter aid
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography (eluting with ethyl acetate:methanol:diethylamine=100:10:5)
  6. additionFractions containing the product
  7. customwere evaporated

Sources & evidence

ORD record
ord-122b88e4a45f443db0f15df5d3f2cd90
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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