Cyanamide → HCID 178503659, compound

HRID 250170Notes

Reaction equation

HRID 250170 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[S:8][C:7]([C:9]([F:12])([F:11])[F:10])=[N:6][CH:5]=1.[N:13]#[C:14][NH2:15].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>ClCCl>[CH3:1][S:2]([CH2:3][C:4]1[S:8][C:7]([C:9]([F:12])([F:10])[F:11])=[N:6][CH:5]=1)=[N:15][C:14]#[N:13]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 12217721Iodo benzene diacetateHCID 59383480HCID 59383480, compound

Product 1

HCID 178503659HCID 178503659, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-[(methylthio)methyl]-2-(trifluoromethyl)-1,3-thiazole (140 mg, 0.62 mmol) and cyanamide (35 mg, 0.83 mmol) in 6 mL of dichloromethane was cooled to 0° C. and treated with iodobenzene diacetate (860 mg, 2.59 mmol). A clear yellow solution was obtained. The mixture was allowed to warm to room temperature over an hour and then the solvent removed under reduced pressure and the residue further purified by flash column chromatography on silica gel using a 50% mixture of acetone and petroleum ether as the eluant. The solvents were removed under reduced pressure to yield 130 mg (83%) of (1E)-methyl{[2-(trifluoromethyl)-1,3-thiazol-5-yl]methyl}-λ4-sulfanylidenecyanamide as a pale yellow syrup: 1H NMR (CDCl3) δ 8.00 (s, 1H), 4.60 (s, 2H), 2.85 (s, 3H); LCMS (ESI) m/z 254 (M+H).

Workup

  1. customA clear yellow solution was obtained
  2. customthe solvent removed under reduced pressure
  3. customthe residue further purified by flash column chromatography on silica gel using a 50% mixture of acetone and petroleum ether as the eluant
  4. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-d74ede8d89b24d6590519fcaa5d36562
Source dataset
uspto-grants-2011_01
Patent number
US07863303B2

Reaction notes

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