Phosgene → HCID 178424800, compound

HRID 1633261Notes

Reaction equation

HRID 1633261 reaction equation
[C:1](Cl)([Cl:3])=O.Cl.Cl.Cl.[NH2:8][C:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][C:10]=1[O:16][CH2:17][CH:18]([OH:32])[CH2:19][NH:20][CH2:21][CH2:22][NH:23][C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:31]>O>[ClH:3].[N:15]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([O:16][CH2:17][CH:18]([OH:32])[CH2:19][NH:20][CH2:21][CH2:22][NH:23][C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:31])[C:9]=2[NH:8][CH:1]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20440405HCID 20440405, compound

Product 1

HCID 178424800HCID 178424800, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosgene is passed into a solution of 21.5 g. 2,3-diamino-1-{2-hydroxy-3-[2-(2,6-dimethylphenylamino)-ethylamino]-propoxy}-benzene trihydrochloride in 400 ml. water for 45 minutes, while cooling (internal temperature 20° to 25° C.). After flushing with nitrogen, the aqueous supernatant is decanted off and the precipitate recrystallized from ethanol/methanol (1:1 v/v), with the addition of active charcoal. There are obtained 6.6 g. (35% of theory) of the desired compound; m.p. 248°-250° C.

Workup

  1. temperaturewhile cooling (internal temperature 20° to 25° C.)
  2. customAfter flushing with nitrogen
  3. customthe aqueous supernatant is decanted off
  4. customthe precipitate recrystallized from ethanol/methanol (1:1 v/v), with the addition of active charcoal
  5. customThere are obtained 6.6 g

Sources & evidence

ORD record
ord-c784cfd601214b7ea4a16d667b9340b4
Source dataset
uspto-grants-1984_10
Patent number
US04479962

Reaction notes

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