Phosgene → HCID 18350625, compound

HRID 430652Notes

Reaction equation

HRID 430652 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][NH:4]1.C(N(CC)CC)C.[C:33](Cl)(Cl)=[O:34]>C1(C)C=CC=CC=1>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([C:6]2[C:7]3[CH:13]=[C:12]4[O:14][CH2:15][O:16][C:11]4=[CH:10][C:8]=3[CH2:9][CH:3]3[CH2:2][O:1][C:33](=[O:34])[N:4]3[N:5]=2)=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 18183107HCID 18183107, compound

Product 1

HCID 18350625HCID 18350625, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.0 g (2.93 mmol) of 8-hydroxymethyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine is mixed in succession with 0.98 ml (7.03 mmol) of triethylamine and 2.23 ml (3.52 mmol) of a 15.6% phosgene solution in toluene while being stirred and cooled. Then, the reaction mixture is heated for 3 hours to 25° C. The precipitate of the crude product is separated, the filtrate is concentrated by evaporation and the residue is treated with water. The combined residues are boiled with ethanol, and after suctioning-off, 0.72 g (67%) of the title compound with a melting point >250° C. (decomposition) is obtained.

Workup

  1. temperaturecooled
  2. temperatureThen, the reaction mixture is heated for 3 hours to 25° C
  3. customThe precipitate of the crude product is separated
  4. concentrationthe filtrate is concentrated by evaporation
  5. additionthe residue is treated with water

Sources & evidence

ORD record
ord-70cdad1abb6541aea59e07db0c788173
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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