Ammonium Chloride → HCID 18537269, compound

HRID 412985Notes

Reaction equation

HRID 412985 reaction equation
FC(F)(F)C(O)=O.[CH3:8][S:9][C:10]1[S:14][C:13]([C:15]([NH2:17])=[NH:16])=[CH:12][C:11]=1[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19].CSC1SC(C(OC)=O)=CC=1S(C1C=CC=CC=1)(=O)=O.[Cl-].[NH4+].C[Al](C)C>C1(C)C=CC=CC=1>[CH3:8][S:9][C:10]1[S:14][C:13]([C:15]([NH2:17])=[NH:16])=[CH:12][C:11]=1[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:19])=[O:20]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 18537031HCID 18537031, compoundHCID 18537479HCID 18537479, compound

Product 1

HCID 18537269HCID 18537269, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Methylthio-4-(phenylsulfonyl)thiophene-2-carboxamidine trifluoroacetate: The same procedure as in Example 257, step (b) was followed using 13.8 mg (0.044 mmol) of methyl 5-methylthio-4-(phenylsulfonyl)thiophene-2-carboxylate (as prepared in the step before), 20 mg of ammonium chloride (0.376 mmol), 0.176 ml of trimethylaluminum (2.0 M in toluene, 0.353 mmol) and 3 ml of anhydrous toluene and chromatographed as before by preparative reverse phase HPLC performed with a Rainin SD-1 Dynamax system and a 2-in. C18 reverse phase Dynamax 60A column using a gradient of 30% MeOH /0.1% TFA in water to 100% MeOH and a flow rate of 50 mL/ min to yield 2.3 mg of 5-methylthio-4-(phenylsulfonyl)thiophene-2-carboxamidine. 1H-NMR (CD3OD, 400 MHz) δ 8.42 (s, 1H), 8.04 (m, 2H), 7.70 (m, 2H), 7.62 (m, 1H) and 2.70 (s, 3H). Mass spectrum (ESI, m/z): Calcd. C12Hi2N2O2S3, 313.0 (M+H), found 313.2.

Workup

  1. customchromatographed as before by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-760a58c7d2f74fc58cd769b6cea507d1
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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