2-(Dimethylamino)acetyl chloride hydrochloride → 4-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)benzene

HRID 258760Notes

Reaction equation

HRID 258760 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]([NH:14][C:15]([O:17][CH3:18])=[O:16])=[S:13].Cl.[CH3:20][N:21]([CH3:26])[CH2:22][C:23](Cl)=[O:24]>CN(C)C=O.C(OCC)C>[CH2:9]([S:8][C:6]1[CH:5]=[CH:4][C:3]([NH:11][C:12]([NH:14][C:15]([O:17][CH3:18])=[O:16])=[S:13])=[C:2]([NH:1][C:23](=[O:24])[CH2:22][N:21]([CH3:26])[CH3:20])[CH:7]=1)[CH3:10]

Participants

5

Reactant 2

HCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 203720472-Amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene

Product 1

HCID 203720164-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)benzeneYield 78.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 2-amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene (8.35 g.) in dry dimethylformamide (60 ml.) was treated at room temperature with N,N-dimethylglycyl chloride hydrochloride (5.53 g.). The mixture was heated to 40°-50° C. for 45 minutes, then cooled, and diluted with diethyl ether (900 ml.). An oil precipitated which crystallised on standing. This solid was filtered off, washed with diethyl ether (100 ml.), and suspended in a mixture of chloroform (100 ml.) and water (100 ml.). Sodium carbonate (3.5 g.) was added and the mixture was stirred for 20 minutes. The chloroform layer was separated and the aqueous layer was extracted twice with chloroform (2× 50 ml.). The organic layers were combined, dried over magnesium sulphate and evaporated to dryness. The residual solid was recrystallised from isopropanol to give 4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)benzene (8.5 g.), m.p. 142° C. (with decomposition).

Workup

  1. temperatureThe mixture was heated to 40°-50° C. for 45 minutes
  2. temperaturecooled
  3. customAn oil precipitated which
  4. customcrystallised
  5. filtrationThis solid was filtered off
  6. washwashed with diethyl ether (100 ml.)
  7. additionsuspended in a mixture of chloroform (100 ml.) and water (100 ml.)
  8. additionSodium carbonate (3.5 g.) was added
  9. customThe chloroform layer was separated
  10. extractionthe aqueous layer was extracted twice with chloroform (2× 50 ml.)
  11. dry with materialdried over magnesium sulphate
  12. customevaporated to dryness
  13. customThe residual solid was recrystallised from isopropanol

Sources & evidence

ORD record
ord-43ddffaf444c43d3833b1dd7b5fbc77c
Source dataset
uspto-grants-1977_07
Patent number
US04034107

Reaction notes

Loading…