Hydrochloric Acid → 1-Ethoxycarbonyl-3-(5-n-butyl-2-dimethylaminoacetamidophenyl)thiourea hydrochloride

HRID 1415642Notes

Reaction equation

HRID 1415642 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=[O:18])[CH2:14][N:15]([CH3:17])[CH3:16].[CH2:19]([O:21][C:22]([N:24]=[C:25]=[S:26])=[O:23])[CH3:20].[ClH:27]>C1C=CC=CC=1.C(O)C.C(OCC)C>[ClH:27].[CH2:19]([O:21][C:22]([NH:24][C:25]([NH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=[O:18])[CH2:14][N:15]([CH3:17])[CH3:16])=[S:26])=[O:23])[CH3:20]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 85320Ethyl isothiocyanatoformateHCID 21482970N-(2-amino-4-n-butylphenyl)-2-dimethylaminoacetamide

Product 1

HCID 1317106281-Ethoxycarbonyl-3-(5-n-butyl-2-dimethylaminoacetamidophenyl)thiourea hydrochloride

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Petroleum spirit (b.p. 60°-80° C; 50 ml) was added to a solution of N-(2-amino-4-n-butylphenyl)-2-dimethylaminoacetamide (4.98 g) in benzene (50 ml) and the solution stirred vigorously while ethoxycarbonyl isothiocyanate (2.65 g) was added dropwise, with external cooling, to maintain the temperature between 15° C. and 20° C. After ten minutes, the precipitated solid was filtered off and recrystallised from benzene to give crude 1-ethoxycarbonyl-3-(5-n-butyl-2-dimethylaminoacetamidophenyl)thiourea, m.p.152°-155° C. (with decomposition), which was then dissolved in the minimum of ethanol. Diethyl ether (200 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/ethyl acetate to give 1-ethoxycarbonyl-3-(5-n-butyl-2-dimethylaminoacetamidophenyl)thiourea hydrochloride (1.9 g), m.p. 174°-176° C. (with decomposition).

Workup

  1. additionwas added dropwise, with external cooling
  2. temperatureto maintain the temperature between 15° C. and 20° C
  3. waitAfter ten minutes
  4. filtrationthe precipitated solid was filtered off
  5. customrecrystallised from benzene
  6. customto give crude 1-ethoxycarbonyl-3-(5-n-butyl-2-dimethylaminoacetamidophenyl)thiourea, m.p.152°-155° C. (with decomposition), which
  7. filtrationThe precipitated solid was filtered off
  8. customrecrystallised from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-a7233c336b484e9596e5b5a53161399f
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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