Ammonium Hydroxide → 2-Cyanimino-3-(4-hydroxy-benzyl)-thiazolidine

HRID 2290262Notes

Reaction equation

HRID 2290262 reaction equation
[C:1]([N:3]=[C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[CH2:7][CH2:6][S:5]1)#[N:2].[OH-].[NH4+]>ClCCl>[C:1]([N:3]=[C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:7][CH2:6][S:5]1)#[N:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 14306204{3-[(4-Methoxyphenyl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide

Product 1

HCID 143062082-Cyanimino-3-(4-hydroxy-benzyl)-thiazolidineYield 0%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.49 g (2 moles) of 2-cyanimino-3-(4-methoxybenzyl)-thiazolidine are dissolved in 12 ml of dichloromethane and a solution of 3.01 g (1.14 ml, 13 mmoles) of borotribromide in 5 ml of dichloromethane is added in an argon atmosphere, dropwise. The mixture is stirred for 12 hours and is then alkalized with an aqueous ammonium hydroxide solution, under stirring and cooling. The phases are separated and the organic phase is evaporated. 0.22 g of 2-cyanimino-3-(4-hydroxy-benzyl)-thiazolidine are obtained in a white crystalline form, melting at 175° to 177° C.

Workup

  1. stirringunder stirring
  2. temperaturecooling
  3. customThe phases are separated
  4. customthe organic phase is evaporated

Sources & evidence

ORD record
ord-381a7baed05e437f92d1bca03ee64567
Source dataset
uspto-grants-1986_10
Patent number
US04616025

Reaction notes

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