Sodium hydride → HCID 66757931, compound

HRID 242553

Reaction equation

HRID 242553 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:33])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31](O)[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:36]1([S:42]([N:45]=[C:46]=[O:47])(=[O:44])=[O:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:33])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31]([C:46](=[O:47])[NH:45][S:42]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)(=[O:43])=[O:44])[C:19]=4[CH2:18]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76096Phenylsulphonyl isocyanateHCID 66757538HCID 66757538, compound

Product 1

HCID 66757931HCID 66757931, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the compound of Example 44 (0.511 g, 1.1 mmol) in dry THF (20 mL) was added sodium hydride (60% in mineral oil, 48 mg, 1.2 mmol), and the slurry heated at 40° C. under argon with stirring for 20 minutes. Phenylsulfonylisocyanate (160 μL, 1.2 mmol) was added and the mixture was stirred for 14 hours. The solvent was then removed by rotary evaporation to give the crude product. The solid material was washed twice with 20 mL CH2Cl2, and then twice with 20 mL MeoH: CH2Cl2 (1:1) to give the title compound (274 mg).

Workup

  1. stirringthe mixture was stirred for 14 hours
  2. customThe solvent was then removed by rotary evaporation
  3. customto give the crude product
  4. washThe solid material was washed twice with 20 mL CH2Cl2

Sources & evidence

ORD record
ord-59b358ccd8934b2287ff0d1b6dc00a52
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Linked notes

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