Hydrochloric Acid → 1-Ethoxycarbonyl-3-(2-dimethylaminoacetamido-5-methoxycarbonylaminophenyl)thiourea hydrochloride

HRID 1415647Notes

Reaction equation

HRID 1415647 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[S:8])=[O:5])[CH3:2].[NH2:9][C:10]1[CH:15]=[C:14]([NH:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[CH:12][C:11]=1[NH:21][C:22](=[O:27])[CH2:23][N:24]([CH3:26])[CH3:25].O.[ClH:29]>CC(C)=O.C(O)C.C(OCC)C>[ClH:29].[CH2:1]([O:3][C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([NH:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[CH:12][C:11]=1[NH:21][C:22](=[O:27])[CH2:23][N:24]([CH3:26])[CH3:25])=[S:8])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 85320Ethyl isothiocyanatoformateHCID 21483024N-(2-amino-4-methoxycarbonylaminophenyl)-2-dimethylaminoacetamide

Product 1

HCID 214830641-Ethoxycarbonyl-3-(2-dimethylaminoacetamido-5-methoxycarbonylaminophenyl)thiourea hydrochloride

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Ethoxycarbonyl isothiocyanate (5.6 g) was added dropwise, with cooling to maintain the temperature between 15° and 20° C., to a vigorously stirred solution of N-(2-amino-4-methoxycarbonylaminophenyl)-2-dimethylaminoacetamide (10.75 g) in dry acetone (200 ml). The resulting mixture was stirred for a further 30 minutes and then poured into an excess of water. The precipitated solid was filtered off to give crude 1-ethoxycarbonyl-3-(2-dimethylaminoacetamido-5-methoxycarbonylaminophenyl)thiourea, m.p. 171°-172° C, which was then 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 methanol/ethanol to give 1-ethoxycarbonyl-3-(2-dimethylaminoacetamido-5-methoxycarbonylaminophenyl)thiourea hydrochloride (7.5 g), m.p. 211°-213° C. (with decomposition).

Workup

  1. temperaturewith cooling
  2. temperatureto maintain the temperature between 15° and 20° C.
  3. filtrationThe precipitated solid was filtered off
  4. customto give crude 1-ethoxycarbonyl-3-(2-dimethylaminoacetamido-5-methoxycarbonylaminophenyl)thiourea, m.p. 171°-172° C, which
  5. filtrationThe precipitated solid was filtered off
  6. customrecrystallised from methanol/ethanol

Sources & evidence

ORD record
ord-a4490ce377cd407aac8bb9c55654f4c0
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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