Dichloromethane → HCID 13885368, compound

HRID 1906345Notes

Reaction equation

HRID 1906345 reaction equation
[N:1]1([S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([NH2:17])(=[O:16])=[O:15])(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.ClCCl.C[Al](C)C.C[O:26][C:27](=O)[NH:28][C:29]1[N:34]=[C:33]([O:35][CH3:36])[N:32]=[C:31]([O:37][CH3:38])[N:30]=1>C1(C)C=CC=CC=1>[N:1]1([S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([NH:17][C:27]([NH:28][C:29]2[N:30]=[C:31]([O:37][CH3:38])[N:32]=[C:33]([O:35][CH3:36])[N:34]=2)=[O:26])(=[O:16])=[O:15])(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 12803256Methyl (4,6-dimethoxy-1,3,5-triazin-2-yl)carbamateHCID 13885367HCID 13885367, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 13885368HCID 13885368, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a dry flask under nitrogen was placed 1.20 gram of 2-(azetidin-1-ylsulfonyl)benzenesulfonamide, 50 ml of dry dichloromethane and 2.48 ml of 2M trimethylaluminum in toluene. To this was added 0.885 g of 4,6-dimethoxy-1,3,5-triazin-2-ylcarbamic acid methyl ester and the resultant solution was heated to reflux for 12 hours. The solution was washed with 50 ml of a water/acetic acid/1N HCl solution (40:10:0.4). The organic fraction was concentrated and chromatographed on silica gel (ethyl acetate/methylene chloride (15:85)). The slower moving portions were collected, treated with ethyl acetate and dried to give 0.45 g of a solid, m.p. 175°-177° C.

Workup

  1. customIn a dry flask under nitrogen was placed
  2. temperatureto reflux for 12 hours
  3. washThe solution was washed with 50 ml of a water/acetic acid/1N HCl solution (40:10:0.4)
  4. concentrationThe organic fraction was concentrated
  5. customchromatographed on silica gel (ethyl acetate/methylene chloride (15:85))
  6. customwere collected
  7. additiontreated with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-4f3b4241939a4f5a9569291fd1fcca74
Source dataset
uspto-grants-1987_03
Patent number
US04652304

Reaction notes

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