Thiourea → HCID 86690823, compound

HRID 1465522Notes

Reaction equation

HRID 1465522 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[CH:7][C:6]=1[CH3:17])=O.[NH2:18][C:19]([NH2:21])=[S:20]>CCO>[CH:14]1([CH2:13][O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]([C:3]3[N:18]=[C:19]([NH2:21])[S:20][CH:2]=3)=[C:6]([CH3:17])[CH:7]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690824HCID 86690824, compound

Product 1

HCID 86690823HCID 86690823, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-(cyclopropylmethoxy)-2,6-dimethylphenyl)ethanone (4-4, 2.06 g, 7.0 mmol) and thiourea (0.61 g, 8.0 mmol) in 95% EtOH (30.0 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (50.0 mL) and saturated aqueous Na2CO3 (1.0 mL). The resultant precipitate was filtered and washed with hot water. The solids were filtered and dried under vacuum to give 4-(4-(cyclopropylmethoxy)-2,6-dimethylphenyl)thiazol-2-amine (4-5, 1.18 g) as yellow solids in 61% yield: 1H NMR (500 MHz, DMSO-d6) δ 9.00 (s, 2 H), 6.73 (s, 2 H), 3.81 (d, J=7.0 Hz, 1 H), 2.10 (s, 6 H), 1.19 (s, 1 H), 0.55 (m, 2 H), 0.30 (m, 2 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (50.0 mL) and saturated aqueous Na2CO3 (1.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with hot water
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-7651c8a43fa449f1b4c02194cf6a4d21
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

Loading…