Triethyl phosphite → HCID 20460466, compound

HRID 543720Notes

Reaction equation

HRID 543720 reaction equation
Br[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4].[CH2:21]([O:23][P:24]([O:28]CC)[O:25][CH2:26][CH3:27])[CH3:22]>>[CH2:21]([O:23][P:24]([CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4])([O:25][CH2:26][CH3:27])=[O:28])[CH3:22]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 20460474HCID 20460474, compound

Product 1

HCID 20460466HCID 20460466, compoundYield 95%

Conditions

Temperature
120 °C

Procedure

A mixture of 143 g (0.43 mol) of 5-bromoacetyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and 400 ml of triethylphosphite was refluxed for 2 hours at 120° C., with stirring. In the course of the reaction, the 5-bromoacetyl compound went fully into solution and a grey precipitate began to settle out. After cooling, this was suction filtered and washed with ethyl acetate and 159 g (95% of theory) of 5-diethylphosphonoacetyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one were obtained; m.p. 195°-197° C.

Workup

  1. customIn the course of the reaction
  2. temperatureAfter cooling
  3. filtrationthis was suction filtered
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ac5d4dcc1e004fe1b90786873d256eb2
Source dataset
uspto-grants-1984_05
Patent number
US04447434

Reaction notes

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