Methanesulfonyl chloride → HCID 14838661, compound

HRID 477495Notes

Reaction equation

HRID 477495 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 109.7%

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 (2.5 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-4ac6ff6cfd9846b89f8c06e3cdc3394f
Source dataset
uspto-grants-1989_12
Patent number
US04888353

Reaction notes

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