Phosgene → HCID 18350625, compound

HRID 1359568Notes

Reaction equation

HRID 1359568 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-b220dbee66244fdd86f9e195e7502b00
Source dataset
uspto-grants-2003_07
Patent number
US06600036B2

Reaction notes

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