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

HRID 2399368Notes

Reaction equation

HRID 2399368 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[Cl:5][C:6]1[CH:20]=[CH:19][C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][NH:14][C:8]=2[CH:7]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)C>[Cl:5][C:6]1[CH:20]=[CH:19][C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]([C:1]([Cl:4])=[O:2])[C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 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 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

8-Chlorodibenz[b,f][1,4]-oxazepine-10(11H)-carbonyl chloride is synthesized in the manner described in U.S. Pat. No. 3,534,019: Phosgene (13 g, 131.4 mmol) in toluene (45 g) is stirred for 2 hours at 5°-10° C. and then diethyl ether (70 g) is added. This is followed by the addition of a solution of 8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine (18.9 g, 81.6 mmol), prepared in the manner described in Example 1, and triethylamine (7.2 g, 9.92 mL, 71.2 mmol) in diethyl ether (140 g). After the addition is complete, the mixture is stirred for 2 hours, and then is filtered. The solvent is then evaporated from the filtrate, and the resulting residue is recrystallized from hexane, giving 8-chlorodibenz[b,f][1,41oxazepine-10(11H)-carbonyl chloride.

Workup

  1. custom8-Chlorodibenz[b,f][1,4]-oxazepine-10(11H)-carbonyl chloride is synthesized in the manner
  2. customprepared in the manner
  3. additionAfter the addition
  4. filtrationis filtered
  5. customThe solvent is then evaporated from the filtrate
  6. customthe resulting residue is recrystallized from hexane

Sources & evidence

ORD record
ord-2d18b65645ab4f1a922cb13c4cde4341
Source dataset
uspto-grants-1995_09
Patent number
US05449674

Reaction notes

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