Triethylamine → HCID 52918808, compound

HRID 2175673Notes

Reaction equation

HRID 2175673 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[CH3:12][O:13][C:14]1[CH:15]=[C:16](/[CH:22]=[CH:23]/[C:24](O)=O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CC#N>[CH3:12][O:13][C:14]1[CH:15]=[C:16](/[CH:22]=[CH:23]/[C:24]2[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8](=[O:9])(=[O:10])[N:11]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 728942-AminobenzenesulfonamideHCID 717531(E)-3,4-Dimethoxycinnamic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 52918808HCID 52918808, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Aminobenzenesulfonamide (0.25 g, 1.4 mmol) was added to a suspension of (E)-3-(3,4-dimethoxyphenyl)acrylic acid (0.25 g, 1.2 mmol), HBTU (0.55 g, 1.4 mmol) and NEt3 (0.67 mL, 4.8 mmol) in MeCN (5 mL) and the reaction was stirred at rt for 16 h. Extra NEt3 (0.67 mL, 4.8 mmol) in MeCN (5 mL) was added and the reaction was stirred at rt for 64 h. The solution was acidified and the precipitate was collected by filtration. Hot EtOH (15 mL) was added to the crude product and the undissolved solid was collected by hot filtration, providing (E)-3-[2-(3,4-dimethoxyphenyl)ethenyl]-4H-1,2,4-benzothiadiazine-1,1-dioxide (58 mg, 14%) as a colourless crystalline solid; mp 276-279° C.; δH (500 MHz, DMSO-d6) 3.81 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 6.75 (d, J=15.6 Hz, 1H, CH═CHCO), 7.05 (d, J5′,6′=8.0 Hz, 1H, H5′), 7.29 (d, J5′,6=8.0 Hz, 1H, H6′), 7.31 (s, 1H, H2′), 7.38 (d, J5,6=8.0 Hz, 1H, H5), 7.45 (t, J5,6=J6,7=8.0 Hz, 1H, H6), 7.68 (t, J6,7=J7,8=8.0 Hz, 1H, H7), 7.80 (d, J7,8=8.0 Hz, 1H, H8), 7.82 (d, J=15.6 Hz, 1H, CH═CHCO), 12.13 (s, 1H, NH); δC (125 MHz, DMSO-d6) 55.4, 55.6, 110.3, 111.8, 116.6, 117.6, 122.0, 122.7, 123.3, 126.3, 126.9, 133.0, 135.2, 142.2, 149.0, 151.1, 153.5; HRMS (ESI) calculated for C17H16N2O4S [M+H]+ 345.0904, found 345.0900; νmax 756, 1134, 1263, 1513, 1568, 1600, 3024, 3117, 3163, 3200 cm−1.

Workup

  1. stirringthe reaction was stirred at rt for 64 h
  2. filtrationthe precipitate was collected by filtration
  3. additionHot EtOH (15 mL) was added to the crude product
  4. filtrationthe undissolved solid was collected by hot filtration

Sources & evidence

ORD record
ord-9eb088484f8c48f182a958d4d09e59b4
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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