18-Crown-6 → HCID 23332702, compound

HRID 224364Notes

Reaction equation

HRID 224364 reaction equation
O1CCOCCOCCOCCOCCOCC1.[F-:19].[K+].[CH:21]1([CH2:24][N:25]2[C:31]3[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:30]=3[C:29]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[N:28][CH:27](OS(C3C=CC(C)=CC=3)(=O)=O)[C:26]2=[O:54])[CH2:23][CH2:22]1>C(#N)C>[CH:21]1([CH2:24][N:25]2[C:31]3[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:30]=3[C:29]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[N:28][CH:27]([F:19])[C:26]2=[O:54])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 23332569HCID 23332569, compound

Product 1

HCID 23332702HCID 23332702, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 5.4 g. of 1,4,7,10,13,16-hexaoxacyclooctadecane dissolved in 50 ml. of dry acetonitrile is added, with stirring, 1.4 g. of anhydrous KF. After 30 minutes, 4.95 g. of 1-cyclopropylmethyl-3-p-toluenesulfonyloxy-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, obtainable by tosylation of the 3-hydroxy compound, in 50 ml. of dry acetonitrile are added. The mixture is stirred for 2 hours more and is worked up in the customary manner to give 1-cyclopropylmethyl-3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one.

Workup

  1. stirringThe mixture is stirred for 2 hours more

Sources & evidence

ORD record
ord-b136f5a28d144e9badc42852be821d79
Source dataset
uspto-grants-1980_11
Patent number
US04232016

Reaction notes

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