Phosgene → HCID 20513300, compound

HRID 1163899Notes

Reaction equation

HRID 1163899 reaction equation
[C:1](Cl)(Cl)=[O:2].Cl.Cl.Cl.[C:8]([C:12]1[CH:13]=[C:14]([NH2:28])[C:15]([NH2:27])=[C:16]([O:18][CH2:19][CH:20]([OH:26])[CH2:21][NH:22][CH:23]([CH3:25])[CH3:24])[CH:17]=1)([CH3:11])([CH3:10])[CH3:9]>>[C:8]([C:12]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]([OH:26])[CH2:21][NH:22][CH:23]([CH3:24])[CH3:25])[C:15]2[NH:27][C:1](=[O:2])[NH:28][C:14]=2[CH:13]=1)([CH3:10])([CH3:9])[CH3:11]

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 20513338HCID 20513338, compound

Product 1

HCID 20513300HCID 20513300, compound

Procedure

Excess phosgene is passed at 20° to 25° C. into a solution of 5.5 g 5-tert.-butyl-2,3-diamino-1-[2-hydroxy-3-(2-propylamino)-propoxy]-benzene trihydrochloride in 50 ml. water, then thoroughly flushed with nitrogen, evaporated and the residue taken up in isopropanol. After a short time 2.3 g. (43% of theory) crystalline 6-tert.-butyl-4-[2-hydroxy-3-(2-propylamino)-propoxy]-2-benzimidazolinone hydrochloride precipitates out; decomposition point above 280° C.

Workup

  1. customwater, then thoroughly flushed with nitrogen
  2. customevaporated
  3. custom(43% of theory) crystalline 6-tert.-butyl-4-[2-hydroxy-3-(2-propylamino)-propoxy]-2-benzimidazolinone hydrochloride precipitates out

Sources & evidence

ORD record
ord-230939eb9768469290374020f76a4749
Source dataset
uspto-grants-1983_01
Patent number
US04367235

Reaction notes

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