Toluene → 8-chlorodibenz[b,f][1,4]oxazepin-10(11H)carbonyl chloride

HRID 1768762Notes

Reaction equation

HRID 1768762 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C1(C)C=CC=CC=1.[Cl:12][C:13]1[CH:27]=[CH:26][C:16]2[O:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[CH2:20][NH:21][C:15]=2[CH:14]=1>CCOCC.C(N(CC)CC)C>[Cl:12][C:13]1[CH:27]=[CH:26][C:16]2[O:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[CH2:20][N:21]([C:1]([Cl:4])=[O:2])[C:15]=2[CH:14]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 152292278-Chloro-10,11-dihydrodibenzo[b,f][1,4]oxazepine

Product 1

HCID 149759838-chlorodibenz[b,f][1,4]oxazepin-10(11H)carbonyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolvent

Procedure

13 parts of phosgene in 45 parts of toluene was stirred for 2 hours at 5°-10° C., and then 70 parts of ether was added. This was followed by the addition of a solution of 18.9 parts of 8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine and 7.2 parts of triethylamine in 140 parts of ether. After the addition was complete, the mixture was stirred for 2 hours, and then was filtered. The solvent was then evaporated from the filtrate. The resulting residue was then dissolved in 200 parts by volume of hot hexane, and this mixture was then filtered and cooled.

Workup

  1. additionAfter the addition
  2. filtrationwas filtered
  3. customThe solvent was then evaporated from the filtrate
  4. dissolutionThe resulting residue was then dissolved in 200 parts by volume of hot hexane
  5. filtrationthis mixture was then filtered
  6. temperaturecooled

Sources & evidence

ORD record
ord-8fa566af05cd41309a89e5dcecfedda4
Source dataset
uspto-grants-1995_01
Patent number
US05378840

Reaction notes

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