Water → 2-(1-Amino-1-methylethyl)-4,5-bis(4-methoxyphenyl)thiazole hydrochloride

HRID 483975Notes

Reaction equation

HRID 483975 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[Cl:11])=[CH:5][CH:4]=1.C(OC([NH:28][C:29]([CH3:34])([CH3:33])[C:30](=[S:32])[NH2:31])=O)(C)(C)C.O>CN(C)C=O>[ClH:11].[NH2:28][C:29]([C:30]1[S:32][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:31]=1)([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 38625232-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-oneHCID 15186362Carbamic acid, (2-amino-1,1-dimethyl-2-thioxoethyl)-, 1,1-dimethylethyl ester

Product 1

HCID 197489022-(1-Amino-1-methylethyl)-4,5-bis(4-methoxyphenyl)thiazole hydrochlorideYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1,2-bis(4-methoxyphenyl)-2-chloroethanone (5.00 g) and 2-tert-butyloxycarbonylamino-2-methylpropanethioamide (4.50 g) in dimethylformamide (25 ml) was stirred at 70° C. for 6 hours. After allowing to cool to the ambient temperature, the reaction mixture was dropped into water. The precipitates were collected by filtration. The resulting residue (6.28 g) was dissolved with dichloromethane (120 ml), and stirred at 2° C. To the reaction mixture was added 1,4-dioxan solution of 4N hydrogen chloride (60 ml), and stirred at ambient temperature for 1 hour. The resulting residue was evaporated in vacuo. The residue was added iso-propyl ether (300 ml) and stirred at 2° C. for 3 hours. The resulting precipitate was collected by filtration and washed with iso-propyl ether, to give 2-(1-amino-1-methylethyl)-4,5-bis(4-methoxyphenyl)thiazole hydrochloride (5.5 g).

Workup

  1. temperatureto cool to the ambient temperature
  2. filtrationThe precipitates were collected by filtration
  3. dissolutionThe resulting residue (6.28 g) was dissolved with dichloromethane (120 ml)
  4. stirringstirred at 2° C
  5. additionTo the reaction mixture was added 1,4-dioxan solution of 4N hydrogen chloride (60 ml)
  6. stirringstirred at ambient temperature for 1 hour
  7. customThe resulting residue was evaporated in vacuo
  8. additionThe residue was added iso-propyl ether (300 ml)
  9. stirringstirred at 2° C. for 3 hours
  10. filtrationThe resulting precipitate was collected by filtration
  11. washwashed with iso-propyl ether

Sources & evidence

ORD record
ord-c0b22498621a4c2cbe4b8f6c1dc95c8a
Source dataset
uspto-grants-1993_07
Patent number
US05229386

Reaction notes

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