Sodium Hydroxide → HCID 15231555, compound

HRID 1081488Notes

Reaction equation

HRID 1081488 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:33]=[CH:32][C:9]2[N:10]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][C:24]=3[O:30][CH3:31])(=[O:22])=[O:21])[C:11](=[O:19])[N:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]=2[CH:7]=1)[CH3:4].Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:36]>O.C1COCC1>[CH2:3]([O:5][C:6]1[CH:33]=[CH:32][C:9]2[N:10]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:35]([O:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:36])=[CH:25][C:24]=3[O:30][CH3:31])(=[O:21])=[O:22])[C:11](=[O:19])[N:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]=2[CH:7]=1)[CH3:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 15231545HCID 15231545, compound

Product 1

HCID 15231555HCID 15231555, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.29 g of NaOH pellets in 2 ml of water was added at 5° C., with stirring, to a solution of 1.1 g of 5-ethoxy-1,3-dihydro-1-(2-methoxy-4-aminobenzenesulfonyl)-3-cyclo-hexyl-2H-benzimidazol-2-one, obtained in Example 5 step B), in 25 ml of THF. 1 ml of phenyl chloroformate was then added with continued stirring. The reaction mixture was then stirred for 5 hours, the temperature being allowed to rise to 20° C. The mixture was then concentrated under vacuum, the residue was taken up with water, extracted with ether and washed with water and the organic phase was dried over sodium sulfate and concentrated under vacuum. 1 g of the expected product was obtained by crystallization from iso ether. M.p.=197° C.

Workup

  1. customto rise to 20° C
  2. concentrationThe mixture was then concentrated under vacuum
  3. extractionextracted with ether
  4. washwashed with water
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1f627eecff814ecf835dffd9561e9307
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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