Ammonia → HCID 67249721, compound

HRID 2358636Notes

Reaction equation

HRID 2358636 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.C[N:22]1CCOCC1.N.O>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:22])=[O:14])=[CH:11][CH:10]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 79724-MethylmorpholineHCID 43349322HCID 43349322, compound

Product 1

HCID 67249721HCID 67249721, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 84a (0.3 g, 1.04 mmol) was dissolved in THF (15 mL) and treated with N-methylmorpholine (0.131 mL, 1.19 mmol) followed by cooling in an ice bath and addition of isobutylchloroforamte (0.148 mL, 1.14 mmol). The resulting mixture was allowed warm to room temperature with stirring for thirty minutes. Subsequent cooling in an ice bath was followed by addition of ammonia gas and warming to room temperature. The title compound was isolated by the addition of water and collection of the solid by vacuum filtration was used without further purification (0.289 g, 96%).

Workup

  1. temperatureby cooling in an ice bath
  2. additionaddition of isobutylchloroforamte (0.148 mL, 1.14 mmol)
  3. temperatureSubsequent cooling in an ice bath
  4. temperaturewarming to room temperature

Sources & evidence

ORD record
ord-0dcb089db7d14ff6923242cba9207668
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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