Methane → HCID 20532148, compound

HRID 1759139Notes

Reaction equation

HRID 1759139 reaction equation
C[Al](C)C.[CH:5]([NH2:8])([CH3:7])[CH3:6].C.[CH3:10][C:11]1[C:16]2[CH2:17][CH2:18][CH2:19][C:15]=2[N:14]=[C:13]([NH:20][C:21]([NH:23][S:24]([C:27]2[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=2[C:29](OC)=[O:30])(=[O:26])=[O:25])=[O:22])[N:12]=1>CCCCCC.C(Cl)Cl.C1(C)C=CC=CC=1>[CH:5]([NH:8][C:29]([C:28]1[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=1[S:24]([NH:23][C:21]([NH:20][C:13]1[N:12]=[C:11]([CH3:10])[C:16]2[CH2:17][CH2:18][CH2:19][C:15]=2[N:14]=1)=[O:22])(=[O:26])=[O:25])=[O:30])([CH3:7])[CH3:6]

Participants

8

Reactant 4

HCID 297MethaneHCID 6363IsopropylamineHCID 13068374HCID 13068374, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 20532148HCID 20532148, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To 21.2 ml of 25% trimethylaluminum in hexane (2.36 molar) under nitrogen is added 2.9 g of isopropyl amine in 100 ml of dried methylene chloride. The mixture is stirred at ambient temperature until evolution of methane gas ceases and then 19.5 g of methyl 2[[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and 200 ml of dry toluene is added. The resulting mixture is heated to distill off the methylene chloride and hexane, after which heating is continued at the reflux temperature of toluene. After 2 hours, the toluene is removed in vacuo, and 200 ml of methylene chloride and 100 ml of 10% hydrochloric acid are added. The phases are separated, and the methylene chloride phase is washed once with water, dried over magnesium sulfate, and filtered, and the methylene chloride distilled to yield the desired compound.

Workup

  1. temperatureThe resulting mixture is heated
  2. distillationto distill off the methylene chloride and hexane
  3. temperatureafter which heating
  4. customthe toluene is removed in vacuo, and 200 ml of methylene chloride and 100 ml of 10% hydrochloric acid
  5. additionare added
  6. customThe phases are separated
  7. washthe methylene chloride phase is washed once with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. distillationthe methylene chloride distilled

Sources & evidence

ORD record
ord-d199d41913e34a3181422763a2f011a3
Source dataset
uspto-grants-1982_07
Patent number
US04339267

Reaction notes

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