Water → HCID 20482448, compound

HRID 648218Notes

Reaction equation

HRID 648218 reaction equation
Cl.Cl.[NH2:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][S:10][C:11](=N)N)[N:8]=1.[CH:14]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33]CCl)[CH2:29][CH2:28]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[Na+]>C(O)C>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][S:10][CH2:11][CH2:33][N:30]2[CH2:31][CH2:32][N:27]([CH:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:28][CH2:29]2)[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 73232Carbamimidothioic acid, (2-amino-4-thiazolyl)methyl ester, hydrochloride (1:2)HCID 4741635HCID 4741635, compound

Product 1

HCID 20482448HCID 20482448, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

S-(2-Aminothiazol-4-ylmethyl)isothiourea dihydrochloride (2.6 g) and 4-benzhydryl-1-(2-chloroethyl)piperazine (3.87 g) were suspended in ethanol (50 ml) in a stream of nitrogen, and thereto was added at a time water (30 ml) containing sodium hydroxide (2.8 g) at ambient temperature with stirring, and the stirring was continued at 50° C. for half an hour. The precipitated crystals were collected by filtration, washed with ethanol and then recrystallized from methanol to give pale yellow crystals (3.0 g) of 2-amino-4-[2-(4-benzhydrylpiperazin-1-yl)ethylthiomethyl]thiazole, mp 159°-161° C.

Workup

  1. waitthe stirring was continued at 50° C. for half an hour
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with ethanol
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4ddc442b6977472484a34a4f50c5074e
Source dataset
uspto-grants-1983_10
Patent number
US04411900

Reaction notes

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