Benzo(d)thiazol-2-amine → 7-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

HRID 1896340Notes

Reaction equation

HRID 1896340 reaction equation
[S:1]1[C:5]2C=CC=C[C:4]=2[N:3]=[C:2]1[NH2:10].[C:11](OCC)(=[O:16])[CH2:12][C:13]([CH3:15])=O>C(O)(=O)C>[CH3:15][C:13]1[N:10]=[C:2]2[S:1][CH:5]=[CH:4][N:3]2[C:11](=[O:16])[CH:12]=1

Participants

4

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 8868Ethyl Acetoacetate

Product 1

HCID 5970657-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-oneYield 40,715.398%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1,3-benzothiazol-2-amine (20 g, 0.133 mmol), ethyl acetoacetate (25.96 g, 0.199 mmol) and acetic acid (150 ml) was reacted together according to the procedure described in Intermediate 3, Step 1 to afford 9 g of the desired product as a pale yellow solid; 1H NMR (300 MHz, CDCl3) δ 2.38 (s, 3H), 6.15 (s, 1H), 6.95 (d, J=4.8 Hz, 1H), 7.94 (d, J=4.8 Hz, 1H).

Sources & evidence

ORD record
ord-945f005dc0104fe58fc755fafa0f1c84
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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