Ammonia → HCID 14856502, compound

HRID 1073330Notes

Reaction equation

HRID 1073330 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[N+]=[N-])[C:4]=2[CH:3]=1.[NH3:17].[S:18](=[O:20])=[O:19].CCCCCC>O1CCCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([S:18]([NH2:17])(=[O:20])=[O:19])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1119Sulfur DioxideHCID 8058HexaneHCID 12871632HCID 12871632, compound

Product 1

HCID 14856502HCID 14856502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (20) (5.3 g, 23.4 mmoL) in tetrahydrofuran was alternately treated with ammonia and sulfur dioxide gas a number of times until TLC (30% EtOAC/hexane) indicated that the starting material had been consumed. The reaction was then concentrated and the residue was diluted with water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic phases were washed with brine (3×100 mL), dried (MgSO4), and concentrated. The crude solid was recrystallized from ethyl acetate/hexane to provide 3.1 (47%) of product (21): mp 190°-194° C.

Workup

  1. customhad been consumed
  2. concentrationThe reaction was then concentrated
  3. additionthe residue was diluted with water (200 mL)
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. washThe combined organic phases were washed with brine (3×100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8dc9bc17e00842f2b771378b459e26f0
Source dataset
uspto-grants-1990_11
Patent number
US04968809

Reaction notes

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