2-Aminothiazole → HCID 43119856, compound

HRID 1809331Notes

Reaction equation

C([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)=O.[NH2:16][C:17]1[S:18][CH:19]=[CH:20][N:21]=1>N1C=CC=CC=1>[S:18]1[CH:19]=[CH:20][N:21]=[C:17]1[NH:16][S:12]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[NH:3][CH2:4][CH2:5]2)(=[O:13])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-formyl-5-(chlorosulfonyl)indoline (60 g, 0.26 mol) and 2-amino thiazole (25 g, 0.26 mol) in pyridine (250 mL) was heated to 60° C. for 1 hour. The reaction mixture was cooled to room temperature and poured into ice/water. The solid was filtered, co-evaporated with toluene until completely dry and used in the next step without further purification. The crude material was brought to reflux in EtOH/KOH (600 mL, 15-20% KOH). After 2 hours a part of the ethanol was removed in vacuo and the light brown precipitate was filtered and crystallized from ethanol. The sulfonamide (39 g, 62% yield) was isolated with a purity of 90% according to HPLC-MS. 1H-NMR (DMSO-d6) δ 7.33-7.30 (m, 2H), 6.87 (d, J=3.8 Hz, 1H), 6.36-6.34 (m, 2H), 5.80 (s, 1H), 3.42 (dt, J=12.0, 4.3 Hz, 2H), 2.88 (t, J=8.5 Hz, 2H).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe solid was filtered
customuntil completely dry
customused in the next step without further purification
temperatureto reflux in EtOH/KOH (600 mL, 15-20% KOH)
customAfter 2 hours a part of the ethanol was removed in vacuo
filtrationthe light brown precipitate was filtered
customcrystallized from ethanol

Sources & evidence

ORD record: ord-beb5b506e86d4fa1a9c9488504145cd8
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362032B2

Reaction notes

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