Sodium hydride → HCID 20524441, compound

HRID 1703001Notes

Reaction equation

HRID 1703001 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH-:8])=[O:7].[C:13]1([CH:19]([O:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=2)[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:8][C:29]([NH:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:20])=[CH:23][CH:24]=1)=[O:30])=[O:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20524446HCID 20524446, compoundHCID 178514229HCID 178514229, compound

Product 1

HCID 20524441HCID 20524441, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.0 g of 50% sodium hydride dispersion in mineral oil was added at room temperature to a solution of 4.0 g of 2-bromobenzoyl amide in 25 ml of dry acetonitrile. After stirring for approximately 30 minutes at room temperature, 4.78 g of 4-(1-phenylethoxy)phenylisocyanate were added, the reaction mixture becoming warm and substantially homogeneous. After stirring for another approximately 16 hours at room temperature the reaction mixture was filtered. The filtrate was acidified with dilute hydrochloric acid. The resulting precipitate was sucked off and washed successively with acetonitrile, ethanol and petroleum ether (40-60). The desired product was obtained in a yield of 1.85 g; the melting point was determined on a "Kofler bank" and was 155.5° C.

Workup

  1. temperaturethe reaction mixture becoming warm
  2. stirringAfter stirring for another approximately 16 hours at room temperature the reaction mixture
  3. filtrationwas filtered
  4. washwashed successively with acetonitrile, ethanol and petroleum ether (40-60)

Sources & evidence

ORD record
ord-29057b0030734d63b126458aae0b1065
Source dataset
uspto-grants-1982_09
Patent number
US04350706

Reaction notes

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