Calcium Carbonate → HCID 67265060, compound

HRID 1685098Notes

Reaction equation

HRID 1685098 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].[Br-:17].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C(=O)([O-])[O-].[Ca+2]>ClCCl.CO>[NH2:1][C:2]1[C:6]([Br:17])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylateHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 67265060HCID 67265060, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 3-amino-5-phenylthiophene-2-carboxylate (2.33 g, 10 mmol) and phenyltrimethylammonium tribromide (9.4 g, 25 mmol) in dichloromethane (25 mL) and methanol (25 mL) was added calcium carbonate (4.03 g, 40 mmol) and the mixture stirred overnight. The solid was filtered off and the filtrate concentrated. The residue was purified by flash chromatography on silica gel using 1:10 ethyl acetate/hexanes to give 2.75 g of the title compound. 1H NMR (DMSO-d6) δ 7.62-7.65 (m, 2H), 7.47-7.51 (m, 3H), 3.80 (s, 3H).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by flash chromatography on silica gel using 1:10 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fbb1510d70e74ad588c2cc0f49e33245
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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