Methyl iodide → HCID 58980898, compound

HRID 1181349Notes

Reaction equation

HRID 1181349 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([S:10][CH3:11])=S)=[CH:4][CH:3]=1.[N:12]#[C:13][NH2:14].C[O-].[K+].CI.[CH3:20][O:21][C:22](=[O:25])CS>CO.CN(C=O)C.CCOC(C)=O.C(N(CC)CC)C>[NH2:12][C:13]1[N:14]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[S:10][C:11]=1[C:22]([O:21][CH3:20])=[O:25]

Participants

10

Reactant 5

HCID 6328Methyl iodideHCID 9864CyanamideHCID 16907Methyl ThioglycolateHCID 12478182HCID 12478182, compoundHCID 23664618Potassium methoxide

Product 1

HCID 58980898HCID 58980898, compoundYield 19%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-chlorobenzenecarbodithioate (0.690, 3.4158 mmol) and cyanamide (0.1436 g, 3.1458 mmol) were taken up in dry methanol (10 mL). Potassium methoxide (0.2396 g, 3.4158 mmol) was added. The reaction was stirred at RT for 3 h. The reaction mixture was concentrated to dryness to give a red solid. The residue was taken up in DMF (10 mL) and methyl iodide (0.727 g, 5.123 mmol) were added. The reaction was stirred for 2 hours, then diluted with EtOAc (50 mL). The organics were washed with water (3×100 mL), dried over MgSO4, filtered and concentrated. The residue was taken up in dry methanol (10 mL) and thioglycolate methyl ester (0.739 g, 9.96 mmol) was added, followed by triethylamine (1.3 mL). The reaction was stirred overnight at RT. The precipitate was collected to give 0.16 g (0.5970 mmol, 17%) of product. 1H NMR (CDCl3) δ 7.85 (d, 2H, J=8.4 Hz), 7.40 (d, 2H, J=8.6 Hz), 5.89 (bs, 2H), 3.85 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customto give a red solid
  3. stirringThe reaction was stirred for 2 hours
  4. washThe organics were washed with water (3×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringThe reaction was stirred overnight at RT
  9. customThe precipitate was collected

Sources & evidence

ORD record
ord-be45104988694cd4a6839408d058814f
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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