Methanesulfonyl chloride → HCID 14838661, compound

HRID 893721Notes

Reaction equation

HRID 893721 reaction equation
C(O)(=O)/C=C/C(O)=O.[NH2:9][C:10]1[CH:18]=[C:17]([C:19]([NH:21][CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][N:24]2[CH2:28][CH3:29])=[O:20])[C:13]2[O:14][CH2:15][CH2:16][C:12]=2[CH:11]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH2:28]([N:24]1[CH2:25][CH2:26][CH2:27][CH:23]1[CH2:22][NH:21][C:19]([C:17]1[C:13]2[O:14][CH2:15][CH2:16][C:12]=2[CH:11]=[C:10]([NH:9][S:31]([CH3:30])(=[O:33])=[O:32])[CH:18]=1)=[O:20])[CH3:29]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19804337HCID 19804337, compound

Product 1

HCID 14838661HCID 14838661, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-amino-N-(1-ethyl-2-pyrrolidinylmethyl)-2,3-dihydrobenzo[b]furan-7-carboxamide (161) (1.80 g, 6.2 mmol) and methanesulfonyl chloride (12.78 g, 0.11 mol) in 30 ml of methylene chloride was heated to reflux overnight. The solution was diluted with CH2Cl2 (30 ml), and then extracted with water (2×30 ml). The combined aqueous layers were made basic with NaHCO3 powder, and extracted with CH2Cl2 (4×50 ml). The organic extracts were combined, dried over anhydrous Na2SO4, and evaporated to give crude 16n (2.25 g, 98.8%). This was recrystallized from EtOH/charcoal to afford 1.70 g of amide as a white solid, mp 180°-182° C.

Workup

  1. temperatureto reflux overnight
  2. extractionextracted with water (2×30 ml)
  3. extractionextracted with CH2Cl2 (4×50 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-24c930598300457092de4462a527bb7d
Source dataset
uspto-grants-1992_06
Patent number
US05126364

Reaction notes

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