Water → HCID 23364238, compound

HRID 1081497Notes

Reaction equation

HRID 1081497 reaction equation
[H-].[Na+].[C:3]12([N:13]3[C:17]4[CH:18]=[C:19]([O:22][CH2:23][CH3:24])[CH:20]=[CH:21][C:16]=4[NH:15][C:14]3=[O:25])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:26][O:27][C:28]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:30][C:29]=1[S:37](Cl)(=[O:39])=[O:38].O>C1COCC1.CN(C=O)C>[C:3]12([N:13]3[C:17]4[CH:18]=[C:19]([O:22][CH2:23][CH3:24])[CH:20]=[CH:21][C:16]=4[N:15]([S:37]([C:29]4[CH:30]=[CH:31][C:32]([N+:34]([O-:36])=[O:35])=[CH:33][C:28]=4[O:27][CH3:26])(=[O:38])=[O:39])[C:14]3=[O:25])[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3094582-Methoxy-4-nitrobenzenesulfonyl chlorideHCID 22922536HCID 22922536, compound

Product 1

HCID 23364238HCID 23364238, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.35 g of sodium hydride as a 60% dispersion in oil is added in portions to a suspension of 2.5 g of 3-(adamant-1-yl)-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one in 10 ml of THF and 20 ml of DMF and the mixture is stirred for 30 minutes at RT. 2.2 g of 2-methoxy-4-nitrobenzenesulfonyl chloride are then added and the formation of a yellow precipitate is observed. The reaction mixture is poured into iced water and the precipitate obtained is filtered off and washed with water, with 95° EtOH and with ether to give 3.8 g of the expected product. M.p.=231° C.

Workup

  1. customthe precipitate obtained
  2. filtrationis filtered off
  3. washwashed with water, with 95° EtOH

Sources & evidence

ORD record
ord-c2fca4e159c4456c92225aefaa08361e
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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