Water → HCID 86672718, compound

HRID 2168544Notes

Reaction equation

HRID 2168544 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][S:6]1(=[O:19])=[O:18].O.FC(F)(F)C(O)=O>C(Cl)Cl>[O:2]=[CH:3][CH2:4][N:5]1[C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][S:6]1(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66898896HCID 66898896, compound

Product 1

HCID 86672718HCID 86672718, compoundYield 148%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of methyl 3-(2,2-dimethoxyethyl)-1,3-dihydro-2,1,3-benzothiadiazole-4-carboxylate 2,2-dioxide (0.2 g, 0.5 mmol) from Step D above in methylene chloride (10 mL) with water (1 mL) and trifluoroacetic acid (0.5 mL) was stirred at room temperature for 3.5 h. The reaction mixture was concentrated under reduced pressure and dried overnight under high vacuum to remove the excess trifluoroacetic acid, providing methyl 3-(2-oxoethyl)-1,3-dihydro-2,1,3-benzothiadiazole-4-carboxylate 2,2-dioxide (0.2 g): 1H NMR (500 MHz, DMSO-d6) δ 9.56 (s, 1H), 7.42 (dd, J=7.5, 1.5 Hz, 1H), 7.19-6.99 (m, 2H), 4.71 (s, 2H), 3.78 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customdried overnight under high vacuum
  3. customto remove the excess trifluoroacetic acid

Sources & evidence

ORD record
ord-574538e75f8c44f1bc9cf4eddbfa21ba
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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