Ammonium Chloride → HCID 86749632, compound

HRID 1734893Notes

Reaction equation

HRID 1734893 reaction equation
C([Li])CCC.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([S:24][CH3:25])[C:14](=[S:21](=[O:23])=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1.I[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:37]([CH3:40])([CH3:39])[CH3:38])=[C:32]([N+:34]([O-:36])=[O:35])[CH:33]=1.[Cl-].[NH4+]>O.C(OCC)C.CN(C)C=O.O1CCCC1.CCCCCC>[C:37]([C:31]1[CH:30]=[CH:29][C:28]([CH2:27][C:13]([C:10]2[CH:9]=[CH:8][C:7]([CH3:6])=[CH:12][CH:11]=2)([S:24][CH3:25])[C:14](=[S:21](=[O:22])=[O:23])[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:33][C:32]=1[N+:34]([O-:36])=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

10

Reactant 4

HCID 25517Ammonium ChlorideHCID 19966029HCID 19966029, compoundHCID 86749633HCID 86749633, compoundHCID 178418339Butyllithium

Product 1

HCID 86749632HCID 86749632, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

3.45 ml (5.52 mmol) of a 1.6M hexane solution of butyllithium was added dropwise over a period of 5 minutes to 10 ml of a tetrahydrofuran solution containing 1.73 g (5.52 mmol) of 1-[2-(4-methylphenyl)-sulfonyl-2-methylthioethyl]hexane (prepared as described in Preparation 8), maintained at -78° C. After 15 minutes, 12 ml of a dimethylformamide solution containing 1.68 g (5.26 mmol) of 5-iodomethyl-2-t-butyl-1-nitrobenzene (prepared as described in Preparation 51) was added dropwise. The reaction mixture was allowed to return to room temperature, after which it was stirred for 1 hour and 20 minutes. At the end of this time, a dilute aqueous solution of ammonium chloride was added, to stop the reaction. Water and diethyl ether were added, and the product was distributed between the organic solvent and water. The organic layer was separated and washed with a saturated aqueous solution of sodium chloride. The solvent was removed by distillation under reduced pressure, to obtain the title compound. Since this compound was unstable, however, it was used for the next step without purification.

Workup

  1. additionwas added dropwise
  2. customto return to room temperature
  3. customthe reaction
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-257c7ee5a9684d4a865994805bdcd33e
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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