Methane → 4-[2-Hydroxy-3-(3,4-dimethoxyphenethylamino)propoxy]-benzimidazoline-2-thione hydrochloride

HRID 67645Notes

Reaction equation

HRID 67645 reaction equation
Cl.Cl.Cl.[NH2:4][C:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH2:13][CH:14]([OH:29])[CH2:15][NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1.[C:30](Cl)([Cl:32])=[S:31].C.Cl>C(O)(C)C.C(Cl)(Cl)Cl.C(O)C>[ClH:32].[OH:29][CH:14]([CH2:15][NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)[CH2:13][O:12][C:6]1[C:5]2[NH:4][C:30](=[S:31])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 10040ThiophosgeneHCID 205275092,3-Diamino-1-[2-hydroxy-3-(3,4-dimethoxyphenethylamino)-propoxy]-benzene trihydrochloride

Product 1

HCID 205275244-[2-Hydroxy-3-(3,4-dimethoxyphenethylamino)propoxy]-benzimidazoline-2-thione hydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent2×

Procedure

17.4 g. 2,3-Diamino-1-[2-hydroxy-3-(3,4-dimethoxyphenethylamino)-propoxy]-benzene trihydrochloride are dissolved in 450 ml. chloroform and 50 ml. ethanol and mixed dropwise at ambient temperature with 3.2 ml. thiophosgene in 30 ml. chloroform. After 2 hours, the reaction mixture is treated with active charcoal and then evaporated to dryness. The residue is purified over a column of silica gel, using chloroform/methanol (8:2 v/v) as elution agent, to give 10 g. (62% of theory) of uniform product. After taking up in isopropanol and mixing with ethereal hydrochloric acid, followed by precipitation by the addition of ethyl acetate, there is obtained 4-[2-hydroxy-3-(3,4-dimethoxyphenethylamino)propoxy]-benzimidazoline-2-thione hydrochloride; m.p. 108°-110° C.

Workup

  1. customevaporated to dryness
  2. customThe residue is purified over a column of silica gel
  3. washas elution agent
  4. customto give 10 g
  5. customfollowed by precipitation by the addition of ethyl acetate

Sources & evidence

ORD record
ord-1ebfd8a7c8d14bea934d859d43c3438b
Source dataset
uspto-grants-1982_08
Patent number
US04346093

Reaction notes

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