1,2-Dichloroethane → HCID 23392185, compound

HRID 990806Notes

Reaction equation

HRID 990806 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([OH:13])=O)=[CH:9][S:8][C:7]=2[CH:14]=1.Cl.[CH3:16][NH:17][O:18][CH3:19].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:19][O:18][N:17]([CH3:16])[C:11]([C:10]1[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:7]=2[S:8][CH:9]=1)=[O:13]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 218271896-Methoxy-1-benzothiophene-3-carboxylic acid

Product 1

HCID 23392185HCID 23392185, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-benzo[b]thiophene-3-carboxylic acid (See Titus, R. L.; Titus, C. F. J. Heterocycl. Chem., 1973, 10, 679-681, incorporated herein by references), (1.2 g, 5.77 mmol) was stirred in dry CH2Cl2 (50 mL) with N,O-dimethyl-hydroxylamine hydrochloride (620 mg, 6.35 mmol). HOBT (1.54 g, 8.08 mmol), EDC (1.54 g, 8.08 mmol), and DIEA (2.16 mL, 12.11 mmol) were added, and the reaction stirred 3 h at r.t. The reaction was diluted with CHCl3 (50 mL) and washed with H2O, 1 N HCI, H2O, saturated NaHCO3, and brine (25 mL each). Organics were dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography (30% to 50% EtOAc/hexanes) gave 952 mg (66%) of 6-methoxy-benzo[b]thiophene-3-carboxylic acid methoxy-methyl amide as a clear oil. 1H NMR (300 MHz, CDCI3) δ8.11 (d, 1H, J=9.0 Hz), 7.89 (s, 1H), 7.31 (d, 1H, J=2.4Hz), 7.06 (dd, 1H, J=9.0, 2.4Hz), 3.88 (s, 3H), 3.61 (s, 3H). 3.40 (s, 3H). Anal. (C12H13NO3S) C, H, N. Calculated C=57.39, H=5.21, N=5.57; found C=57.39, H=5.11, N=5.57.

Workup

  1. washwashed with H2O, 1 N HCI, H2O, saturated NaHCO3, and brine (25 mL each)
  2. dry with materialOrganics were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel chromatography (30% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ea45fd9d0eb542909f9293bb8c2677cd
Source dataset
uspto-grants-2002_10
Patent number
US06462069B2

Reaction notes

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