Sodium hydride → HCID 14402884, compound

HRID 1381819Notes

Reaction equation

HRID 1381819 reaction equation
[H-].[Na+].[F:3][C:4]1[C:14]([N:15]2[C:23](=[O:24])[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16]2=[O:25])=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1.Cl[CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O.[I-].[Na+].C1OCCOCCOCCOCCOCCOC1>[F:3][C:4]1[C:14]([N:15]2[C:23](=[O:24])[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16]2=[O:25])=[CH:13][C:7]2[N:8]([CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 75361Silane, (chloromethyl)trimethyl-HCID 137721852-(7-Fluoro-3-oxo-4H-1,4-benzoxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione

Product 1

HCID 14402884HCID 14402884, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent2×

Procedure

To N,N-dimethylformamide (10 ml) is added at an ambient temperature sodium hydride (0.1 g), sodium iodide (5 mg), 18-crown-6 (5 mg) and 2-[7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.63 g). Thereafter the whole is stirred for 15 minutes, treated with a solution of chloromethyltrimethylsilane (0.61 g) in N,N-dimethylformamide (5 ml), and stirred at 100°-110° C. for an hour. The reaction mixture is evaporated to dryness in vacuo, admixed with water (30 ml), and extracted twice with dichloromethane (30 ml). The combined extract is dried over sodium sulfate and evaporated in vacuo to obtain an oily end product 2-[7-fluoro-4-trimethylsilylmethyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.7 g). nD20 1.5596.

Workup

  1. stirringstirred at 100°-110° C. for an hour
  2. customThe reaction mixture is evaporated to dryness in vacuo
  3. extractionextracted twice with dichloromethane (30 ml)
  4. extractionThe combined extract
  5. dry with materialis dried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8bbc8ba8f2d648ea87511a5ef7a4723a
Source dataset
uspto-grants-1989_02
Patent number
US04804394

Reaction notes

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