Sodium hydride → HCID 20392242, compound

HRID 1863170Notes

Reaction equation

HRID 1863170 reaction equation
[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5]2.[H-].[Na+].[CH2:18](I)[CH2:19][CH3:20]>CN(C)C=O>[CH2:18]([N:8]1[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[NH:5][C:4]2=[CH:3][S:2][CH:1]=[C:10]2[C:9]1=[O:11])[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 20392242HCID 20392242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An 11.8 g. portion of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 2.8 g. of 50% sodium hydride in mineral oil in 175 ml. of dimethylformamide is stirred for 2 hours. A 12.6 g. portion of n-propyl iodide is added and the mixture is stirred overnight at room temperature. The reaction mixture is poured into ice water. After 3 hours the brown crystals are recovered by filtration, washed thoroughly with water, then ether and dried. This solid is heated to boiling in 75 ml. of methanol, filtered while hot and the filtrate is stored in a chill room. The crystals which form are recovered by filtration, washed with ether and dried giving the desired product, mp. 166°-167° C.

Workup

  1. filtrationAfter 3 hours the brown crystals are recovered by filtration
  2. washwashed thoroughly with water
  3. dry with materialether and dried
  4. temperatureThis solid is heated
  5. filtrationof methanol, filtered while hot and the filtrate
  6. customThe crystals which form
  7. filtrationare recovered by filtration
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-26c61beff5484f58b64f1ea1265718d0
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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