Sodium Bicarbonate → 2-Amino-4-methyl-thiazole-5-sulfonic acid (2-dimethylamino-ethyl)-amide

HRID 900882Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][NH:5][S:6]([C:9]1[S:13][C:12]([NH:14]C(=O)C)=[N:11][C:10]=1[CH3:18])(=[O:8])=[O:7].C([O-])(O)=O.[Na+]>Cl>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][NH:5][S:6]([C:9]1[S:13][C:12]([NH2:14])=[N:11][C:10]=1[CH3:18])(=[O:8])=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred suspension of 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-dimethylamino-ethyl)-amide (1.0 g, 3.26 mmol) in 6N hydrochloric acid (13 ml) was heated for 2 h at 80° C., and 2N NaHCO3 solution (100 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml), the combined organic layers washed with brine (50 ml) and dried (MgSO4). The crude product was further purified by crystallization (ethyl aceate) to yield the title compound (0.68 g, 79%) as a white solid. MS (ISP) 262.9 [(M−H)−]; mp 153° C.

Workup

extractionThe mixture was extracted with ethyl acetate (3×50 ml)
washthe combined organic layers washed with brine (50 ml)
dry with materialdried (MgSO4)
customThe crude product was further purified by crystallization (ethyl aceate)

Sources & evidence

ORD record: ord-be4e547b00c84bfb829f5337763c3a8f
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361659B2

Reaction notes

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