2,2-Diethoxyethylamine → HCID 178467951, compound

HRID 1763557Notes

Reaction equation

HRID 1763557 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([NH:12][C:13](=[NH:16])SC)[CH2:7][CH2:6]2.[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21][NH2:22])[CH3:18]>>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([NH:12][C:13]([NH:22][CH2:21][CH:20]([O:23][CH2:24][CH3:25])[O:19][CH2:17][CH3:18])=[NH:16])[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 178504055HCID 178504055, compound

Product 1

HCID 178467951HCID 178467951, compound

Procedure

6 g of 1-(5-chlorindolin-1yl)-2-methylisothiourea hydrochloride and 10 ml of aminoacetaldehyde diethyl acetal were heated to a bath temperature of 120° for 1 hour. The excess aminoacetaldehyde diethyl acetal was removed by evaporation in a vacuum and the evaporation residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution. The organic phase was dried over magnesium sulphate and was evaporated to dryness. The 1-(5-chloroindolin-1-yl)-3-(2,2-diethoxyethyl)guanidine obtained as the evaporation residue was crystallized as the naphthalene-1,5-disulphonate having a M.Pt. of 163° -165° (from ethanol/ether).

Workup

  1. customThe excess aminoacetaldehyde diethyl acetal was removed by evaporation in a vacuum
  2. customthe evaporation residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-1ffd67128c2f432eb8667028fce3500a
Source dataset
uspto-grants-1978_09
Patent number
US04112111

Reaction notes

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