Dimethylamine → HCID 21483012, compound

HRID 1415652Notes

Reaction equation

HRID 1415652 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][O:5][C:6]([NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](=[O:23])[CH2:20][CH2:21][Cl:22])=[S:10])=[O:7]>C(O)C>[ClH:22].[CH3:4][O:5][C:6]([NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](=[O:23])[CH2:20][CH2:21][N:2]([CH3:3])[CH3:1])=[S:10])=[O:7]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 21482999HCID 21482999, compound

Product 1

HCID 21483012HCID 21483012, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of dimethylamine in ethanol (20% w/w; 18 ml) was added to a suspension of 1-methoxycarbonyl-3-[2-(3-chloropropionamido)phenyl]thiourea (8.2 g) in ethanol (50 ml). The mixture was heated under reflux, with stirring, for 30 minutes, the ethanol removed by distillation and water (10 ml) added to the residual gum which slowly solidified. The solid was filtered off and dissolved in the minimum of ethanol. Diethyl ether (300 ml) was added, followed by an excess of a saturated solution of hydrogen chloride in diethyl ether. The precipitated solid was filtered off and recrystallised from ethanol to give 1-methoxycarbonyl-3-[2-(3-dimethylaminopropionamido)phenyl]thiourea hydrochloride (3.3 g), m.p. 182°-183° C. (with decomposition).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customthe ethanol removed by distillation and water (10 ml)
  4. additionadded to the residual gum which
  5. filtrationThe solid was filtered off
  6. dissolutiondissolved in the minimum of ethanol
  7. additionDiethyl ether (300 ml) was added
  8. filtrationThe precipitated solid was filtered off
  9. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-4dc47f78d16e4d0a9a2006b0022388db
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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