Iodoethane → HCID 20392234, compound

HRID 1863163Notes

Reaction equation

HRID 1863163 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)[CH3:19]>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])[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 20392234HCID 20392234, 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 is reacted with 2.8 g. of 50% sodium hydride in mineral oil in 175 ml. of dimethylformamide. After 2 hours 11.5 g. of ethyl 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 collected, washed with water and then ether and dried. The solid is heated to boiling in 75 ml. of methanol, filtered and the filtrate is treated with charcoal, reheated to the boil and filtered through diatomaceous earth. To the filtrate is added, portionwise with swirling, 100 ml. of water. The mixture is cooled in a chill room and the solid is collected, washed with ether and dried giving the desired product, mp. 175°-177° C.

Workup

  1. customAfter 3 hours the brown crystals are collected
  2. washwashed with water
  3. dry with materialether and dried
  4. temperatureThe solid is heated
  5. filtrationof methanol, filtered
  6. additionthe filtrate is treated with charcoal
  7. filtrationfiltered through diatomaceous earth
  8. additionTo the filtrate is added
  9. temperatureThe mixture is cooled in a chill room
  10. customthe solid is collected
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-79d89e9733ee4a8d913bc6ccf92488f5
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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