Sodium Carbonate → HCID 23353368, compound

HRID 235058Notes

Reaction equation

HRID 235058 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]#[N:11].[C:12]([O:16][CH3:17])(=[O:15])[CH2:13][SH:14].C([O-])([O-])=O.[Na+].[Na+]>CO>[NH2:11][C:10]1[C:3]2[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=2[S:14][C:13]=1[C:12]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 16907Methyl ThioglycolateHCID 30142761,3-Benzenedicarbonitrile, 4-chloro-

Product 1

HCID 23353368HCID 23353368, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloroisophthalonitrile (5.69 g, 35 mmol), prepared by the method of Markley et al, J. Med. Chem., 29: 427 (1986), was treated with 1 equivalent methyl thioglycolate and 1 equivalent Na2CO3 in methanol by the procedure described in Example 41A to yield the title compound (3.00 g, 37%). m.p. 248° C. 1H NMR (300 MHz, DMSO) δ 8.71 (s, 1H), 8.09 (d, 1H), 7.86 (dd, 1H), 7.30 (br s, 2H), 3.81 (s, 3H). MS (DCI/NH3) m/e 250 (M+NH4)+.

Sources & evidence

ORD record
ord-935550485dd1473d9f2dec2261da8958
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

Loading…