Thiourea → 4-(4-Chlorobenzyl)thiazol-2-amine

HRID 2401783Notes

Reaction equation

HRID 2401783 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[NH2:13][C:14]([NH2:16])=[S:15]>C(O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]2[N:13]=[C:14]([NH2:16])[S:15][CH:2]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 147488551-Bromo-3-(4-chlorophenyl)propan-2-one

Product 1

HCID 116515014-(4-Chlorobenzyl)thiazol-2-amineYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-bromo-3-(4-chlorophenyl)propan-2-one (25.4 grams, 103 mmol) and thiourea (8.59 g, 113 mmol) in ethanol (1.51 L) was heated at 85° C. for 2 hours. The reaction was cooled and concentrated in vacuo and the residue was taken up in ethyl acetate (300 mL) and saturated sodium bicarbonate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was recrystallized from ethyl acetate/hexanes to give 19.9 grams of the title compound as a tan powder (86% yield). LC/MS (FA) ES+ 225. 1H NMR (300 MHz, CDCl3) δ: 7.29-7.24 (m, 2H), 7.20-7.15 (m, 2H), 6.04 (m, 1H), 5.00 (bs, m, 2H), 3.83 (s, 2H).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
  5. washThe combined organic layers were washed with brine (50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d5f3151751634c669bf29236dbccfee8
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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