Potassium Carbonate → HCID 9835167, compound

HRID 1797771Notes

Reaction equation

HRID 1797771 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=O)=[CH:5][CH:4]=1.[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([NH2:21])=[C:18]([SH:20])[CH:19]=1.C([O-])([O-])=O.[K+].[K+]>>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[N:21]=[C:7]([C:6]3[CH:10]=[CH:11][C:3]([NH:2][CH3:1])=[CH:4][CH:5]=3)[S:20][C:18]=2[CH:19]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 663454-(Methylamino)benzoic acidHCID 2355092-Amino-5-methoxybenzene-1-thiol

Product 1

HCID 9835167HCID 9835167, compoundYield 22.3%

Conditions

Temperature
170 °C

Procedure

A mixture of 4-methylaminobenzoic acid (11.5 g, 76.2 mmol) and 5-methoxy-2-aminothiophenol (12.5, g, 80 mmol) was heated in PPA (˜30 g) to 170° C. under N2 atmosphere for 1.5 hr. The reaction mixture was then cooled to room temperature and poured into 10% K2CO3 solution. The precipitate was filtered under reduced pressure. The crude product was re-crystallized twice from acetone/water and THF/water followed by the treatment with active with carbon to give 4.6 g (21%) of 6-Methoxy-2-(4-methylaminophenyl)benzothiazole as a yellow solid. 1HNMR (300 MHz, acetone-d6) δ: 7.84(d, J=8.7 Hz, 2H, H-2′6′), 7.78(dd, J1=8.8 Hz, J2=1.3 Hz, 1H, H-4), 7.52(d, J=2.4 Hz, 1H, H-7), 7.05(dd, J1=8.8 Hz, J2=2.4 Hz, H-5), 6.70(d, J=7.6 Hz, 2H, H-3′5′), 5.62(s, 1H, NH), 3.88(s, 3H, OCH3), 2.85(d, J=6.2 Hz, 3H, NCH3)

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationThe precipitate was filtered under reduced pressure
  3. customThe crude product was re-crystallized twice from acetone/water and THF/water

Sources & evidence

ORD record
ord-7af7890c75b242418a7febe3679e6906
Source dataset
uspto-grants-2013_01
Patent number
US08343457B2

Reaction notes

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