p-Toluenesulfonic acid → 2-(1,3-Thiazol-2-yl)propan-2-amine

HRID 631973Notes

Reaction equation

HRID 631973 reaction equation
[NH2:1][C:2](=[S:14])[C:3]([NH:6]C(=O)OC(C)(C)C)([CH3:5])[CH3:4].Br[CH2:16][CH:17](OC)OC.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[CH3:5][C:3]([CH3:4])([C:2]1[S:14][CH:16]=[CH:17][N:1]=1)[NH2:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 15186362Carbamic acid, (2-amino-1,1-dimethyl-2-thioxoethyl)-, 1,1-dimethylethyl ester

Product 1

HCID 282862032-(1,3-Thiazol-2-yl)propan-2-amineYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tert-butyl 1-amino-2-methyl-1-thioxopropan-2-ylcarbamate (5.31 g, 24 mmol), 2-bromo-1,1-dimethoxyethane (CAN:7252-83-7, 5.11 g, 30 mmol) and TsOH (0.49 g, 3 mmol) in acetic acid (50 mL) was stirred at 120° C. for 4 h. After evaporation of solvents, the residue was diluted with ethyl acetate (50 mL) and water (50 mL). The water phase was washed with ethyl acetate (3×50 mL). Then water phase was lyophilized to give the title compound as brown solid (2.1 g, 65%); MS (LC/MS): 143.1 [M+H]+.

Workup

  1. customAfter evaporation of solvents
  2. additionthe residue was diluted with ethyl acetate (50 mL) and water (50 mL)
  3. washThe water phase was washed with ethyl acetate (3×50 mL)

Sources & evidence

ORD record
ord-cfc252bca8f1485c8979cc6e89b6f9d1
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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