Methyl thiophene-2-carbimidothioate hydroiodide → HCID 178465426, compound

HRID 1668500Notes

Reaction equation

HRID 1668500 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:16][CH2:15][CH:14]([N:17]([CH2:25][CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH:12]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.I.CS[C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[NH:31]>CCO>[CH2:25]([N:17]([CH:14]1[CH2:15][CH2:16][C:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([NH:1][C:30]([C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)=[NH:31])=[CH:3][CH:4]=3)[NH:8][CH:7]=2)=[CH:12][CH2:13]1)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH3:26]

Participants

4

Reactant 2

HCID 66704664Methyl thiophene-2-carbimidothioate hydroiodideHCID 68254813HCID 68254813, compound

Product 1

HCID 178465426HCID 178465426, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of above compound 130 in dry EtOH (5 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.29 g, 1.037 mmol) at room temperature and stirred for 24 h. Solvent was evaporated and crude was diluted with sat. NaHCO3 solution (20 mL) and product was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layer washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95) to obtain compound 131 (0.18 g, 75%, over two steps) as a yellow solid. mp 110-112° C.; 1H NMR (DMSO-d6) δ 1.09 (t, 3H, J=6.6 Hz), 1.42 (s, 9H), 1.82-1.93 (m, 2H), 2.22-2.64 (m, 4H), 3.12-3.18 (m, 2H), 4.06 (brs, 1H), 6.10 (s, 1H), 6.32 (s, 2H), 6.60 (d, 1H, J=8.4 Hz), 6.82 (s, 1H), 7.09 (t, 1H, J=4.5 Hz), 7.23 (s, 1H), 7.59 (d, 1H, J=4.8 Hz), 7.68-7.73 (m, 2H), 10.84 (s, 1H); ESI-MS (m/z, %) 465 (MH+, 100).

Workup

  1. customSolvent was evaporated
  2. additioncrude was diluted with sat. NaHCO3 solution (20 mL) and product
  3. extractionwas extracted into CH2Cl2 (2×20 mL)
  4. washThe combined CH2Cl2 layer washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-dba117014ab04677938ff64bc93ca59c
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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