Dimethylamine → 1-Methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea hydrochloride

HRID 1415636Notes

Reaction equation

HRID 1415636 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:19])[CH2:17][Cl:18])=[S:7])=[O:4].[CH3:20][NH:21][CH3:22]>C1C=CC=CC=1>[ClH:18].[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:19])[CH2:17][N:21]([CH3:22])[CH3:20])=[S:7])=[O:4]

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 214518911-Methoxycarbonyl-3-(2-chloroacetamidophenyl)thiourea

Product 1

HCID 212695831-Methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A suspension of 1-methoxycarbonyl-3-(2-chloroacetamidophenyl)thiourea (1.51 g) in benzene (50 ml) was treated with a solution of dimethylamine in benzene (15 ml., 10% w/w). The mixture was heated to reflux for 15 minutes with stirring. A further quantity of dimethylamine in benzene (5ml, 10% w/w) was added, and the mixture heated to reflux for a further 15 minutes with stirring. The mixture was allowed to stand for 1 hour, during which time it cooled to room temperature, and was then filtered. The filtrate was treated with an excess of a saturated solution of hydrogen chloride in diethyl ether. The precipitate was filtered off, treated with water (20 ml), some insoluble solid was filtered off, and the aqueous filtrate neutralised by treatment with 2N aqueous sodium hydroxide solution. The resultant solid was filtered off, dissolved in the minimum quantity of ethanol and the solution treated with diethyl ether, followed by an excess of a saturated solution of hydrogen chloride in diethyl ether. The resultant solid was filtered off and recrystallised from ethanol to give 1-methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea hydrochloride (0.25 g), m.p. 187°-188° C. (with decomposition).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 minutes
  3. temperaturethe mixture heated
  4. temperatureto reflux for a further 15 minutes
  5. stirringwith stirring
  6. filtrationwas then filtered
  7. additionThe filtrate was treated with an excess of a saturated solution of hydrogen chloride in diethyl ether
  8. filtrationThe precipitate was filtered off
  9. additiontreated with water (20 ml)
  10. filtrationsome insoluble solid was filtered off
  11. filtrationThe resultant solid was filtered off
  12. dissolutiondissolved in the minimum quantity of ethanol
  13. additionthe solution treated with diethyl ether
  14. filtrationThe resultant solid was filtered off
  15. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-b48e178f5ad64a24b8ba71bf40602f69
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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