Hydrochloric Acid → 4-methoxy-5-(N-(2-morpholinoethyl)-methylsulfonamido)thiophene-2-carboxylic acid hydrochloride

HRID 59756Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:21]([O:23]CC)=[O:22])[S:6][C:7]=1[N:8]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[S:9]([CH3:12])(=[O:11])=[O:10].[ClH:26]>O1CCOCC1>[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:21]([OH:23])=[O:22])[S:6][C:7]=1[N:8]([CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[S:9]([CH3:12])(=[O:10])=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 4-methoxy-5-(N-(2-morpholinoethyl)-methylsulfonamido)-thiophene-2-carboxylate (Int. 70, 375 mg, 0.955 mmol) (prepared as described in Step 6 hereabove reported) in dioxane (8 ml), aqueous 37% HCl (3 ml) was added drop wise, and the resulting mixture was heated under MW irradiation at 100° C. for 3.5 hours. The volatiles were removed under vacuum to afford 4-methoxy-5-(N-(2-morpholinoethyl)-methylsulfonamido)thiophene-2-carboxylic acid hydrochloride (Int. 71) (383 mg, 0.955 mmol, MS/ESI+364.9 [MH]+).

Workup

customThe volatiles were removed under vacuum

Sources & evidence

ORD record: ord-13d8149d02f44a0abbccd76f0b249bb4
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440954B2

Reaction notes

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