Ethyl isothiocyanatoformate → 1-Ethoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea

HRID 1415638Notes

Reaction equation

HRID 1415638 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[CH2:10][N:11]([CH3:13])[CH3:12].[CH2:15]([O:17][C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH3:16]>C(#N)C>[CH2:15]([O:17][C:18]([NH:20][C:21]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[CH2:10][N:11]([CH3:12])[CH3:13])=[S:22])=[O:19])[CH3:16]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 16784338N-(2-aminophenyl)-2-(dimethylamino)acetamide

Product 1

HCID 214829821-Ethoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thioureaYield 62.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of N-(2-aminophenyl)-2-dimethylaminoacetamide (8.9 g) (prepared as described in Example 6) in acetonitrile (50 ml) was treated with ethoxycarbonyl isothiocyanate (6.4 g), dropwise with stirring, maintaining the temperature at 15°-20° C. by external cooling. When the addition was complete, the solid had dissolved but after being left to stand for a further 5 minutes, another solid precipitated. This was filtered off and washed with ice-cold acetonitrile to give 1-ethoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea (9.4 g), m.p. 159°-160° C. (with decomposition).

Workup

  1. temperaturemaintaining the temperature at 15°-20° C. by external cooling
  2. additionWhen the addition
  3. dissolutionthe solid had dissolved
  4. waitafter being left
  5. customanother solid precipitated
  6. filtrationThis was filtered off
  7. washwashed with ice-cold acetonitrile

Sources & evidence

ORD record
ord-dad36edf293c4c5eaabc06dca4f775b0
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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