O-Phenylenediamine → HCID 135843665, compound

HRID 49001Notes

Reaction equation

HRID 49001 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21](=O)[C:22](OC)=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH2:36]>C(O)C>[O:23]=[C:22]1[NH:36][C:31]2[C:30](=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:29]=[C:21]1[C:18]1[C:17]2[CH:27]=[C:13]([N:4]3[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:11])([F:9])[F:10])[N:2]([CH3:1])[C:3]3=[O:28])[CH:14]=[CH:15][C:16]=2[S:20][N:19]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 20634280Methyl 5-[3-,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-glyoxylate

Product 1

HCID 135843665HCID 135843665, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 5-[3-,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-glyoxylate (0.7500 g, 1.81 mmol), 1,2-diaminobenzene (0.200 g, 1.84 mmol) and ethanol is stirred 16 hours at reflux and filtered hot. The filtrate is concentrated in vacuo to afford the title compound as a light yellow solid (0.480 g, 56.3%, mp >250° C.) which is identified by NMR analysis.

Workup

  1. temperatureat reflux
  2. filtrationfiltered hot
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-8f09a812df7c40d2bd21f2c60862547c
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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