Methyl isothiocyanate → 1-Methyl-3-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]thiourea

HRID 1455074Notes

Reaction equation

HRID 1455074 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[N:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][N:26]=[C:27]=[S:28]>C(O)C>[CH3:25][NH:26][C:27]([NH:24][C:21]1[CH:22]=[N:23][C:18]([O:17][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[O:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15]3)=[CH:19][CH:20]=1)=[S:28]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridine

Product 1

HCID 179786351-Methyl-3-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solution of 6-(2-phenylchroman-6-yloxy)pyridin-3-ylamine (150 mg) and methyl isothiocyanate (94 μl) in ethanol was refluxed for 10 hours. After cooling solvents were evaporated. Crude product of 1-methyl-3-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]thiourea was purified by column chromatography (5% methanol in dichloromethane). 1H NMR (400 MHz, d6-DMSO) δ: 9.45 (bs, 1H), 8.02 (d, 1H, J 2.7 Hz), 7.81 (dd, 1H, J 2.7, 8.8 Hz), 7.70 (bs, 1H), 7.47-7.38 (m, 4H), 7.36-7.32 (m, 1H), 6.94-6.86 (m, 4H), 5.12 (dd, 1H J 2.3, 10.1 Hz), 2.98-2.93 (m, 1H), 2.90 (d, 3H, J 4.3 Hz), 2.76-2.71 (m, 1H), 2.19-2.15 (m, 1H), 2.15-1.99 (m, 1H).

Workup

  1. temperatureAfter cooling solvents
  2. customwere evaporated
  3. customCrude product of 1-methyl-3-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]thiourea was purified by column chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-03bfe4636b5f4b1e9a775e4b9efb8884
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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