Calcium Carbonate → HCID 54186567, compound

HRID 1459698Notes

Reaction equation

HRID 1459698 reaction equation
[I:1]Cl.[N:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[Ca+2]>CO>[I:1][C:10]1[CH:9]=[C:8]([N:6]2[CH:5]=[N:4][N:3]=[CH:7]2)[CH:13]=[CH:12][C:11]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 54494012HCID 54494012, compound

Product 1

HCID 54186567HCID 54186567, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of iodine monochloride (22.3 g, 137 mmol) in methanol (300 ml) was added over 0.75 h to a stirred suspension of 4-(1,2,4-triazol-4-yl)phenylaniline (20.0 g, 125 mmol) and calcium carbonate (25.0 g, 250 mmol) in methanol (800 ml) at -30° C. under nitrogen. The mixture was allowed to warm to room temperature and stirred for 16 h before filtering through a pad of celite. The filtrate was evaporated in vacuo and the residue dissolved in EtOAc and washed with 50% wlw sodium bisulphite solution. The solid material was filtered off and the organic layer dried (MgSO4), evaporated in vacuo and combined with the solid material to give the title product (23.9 g, 67%), δ (250 MHz, d6 -DMSO) 5.54 (2H, br s, NH2), 6.84 (1H, d, J=8.7 Hz, Ar--H), 7.38 (1H, dd, J=2.6 and 8.7 Hz, Ar--H), 7.87 (1H, d, J=2.5 Hz, Ar--H), 8.92 (2H, s, Ar--H).

Workup

  1. filtrationbefore filtering through a pad of celite
  2. customThe filtrate was evaporated in vacuo
  3. dissolutionthe residue dissolved in EtOAc
  4. washwashed with 50% wlw sodium bisulphite solution
  5. filtrationThe solid material was filtered off
  6. dry with materialthe organic layer dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4a5e733b80f44680b9f87a5cfa428703
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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