Iodine → 3-Iodo-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazol-4-one

HRID 1642407Notes

Reaction equation

HRID 1642407 reaction equation
II.ClC1C=CC(/C=[CH:11]/[C:12]2[N:13]=[C:14]3[S:22][CH:21]=[CH:20][N:15]3[C:16](=[O:19])[C:17]=2[I:18])=CC=1>C(#N)C>[I:18][C:17]1[C:16](=[O:19])[N:15]2[C:14]([S:22][C:21]3[CH:16]=[CH:17][CH:12]=[CH:11][C:20]=32)=[N:13][C:12]=1[CH3:11]

Participants

4

Reactant 2

HCID 807IodineHCID 66753972HCID 66753972, compound

Product 1

HCID 667535103-Iodo-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazol-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of the Step 1 intermediate (9 g, 41.613 mmol) in acetonitrile (150 ml) was reacted with ceric ammonium nitrate (11 g, 20.803 mmol) followed by iodine (6 g, 24.961 mmol) according to the procedure outlined in Intermediate 1, Step 3 to give 9 g of the product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) 1H NMR (300 MHz, DMSO-d6) δ 3.15 (s, 3H), 7.54-7.60 (m, 2H), 8.00-8.07 (m, 1H), 8.84-8.90 (m, 1H).

Sources & evidence

ORD record
ord-517a9ed8d3e04a93b4aad6b63f8992ab
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

Loading…