Allyl isocyanate → 3-Oxo-3H-benzo[d]isothiazole-2-carboxylic acid allylamide

HRID 736618

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[O:10])[NH:2]1.[CH2:11]([N:14]=[C:15]=[O:16])[CH:12]=[CH2:13]>>[CH2:11]([NH:14][C:15]([N:2]1[C:3](=[O:10])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1]1)=[O:16])[CH:12]=[CH2:13]

Participants

Reactant 2

HCID 15123Allyl isocyanate

HCID 175201,2-Benzisothiazol-3(2H)-one

Product 1

HCID 113108623-Oxo-3H-benzo[d]isothiazole-2-carboxylic acid allylamide

Procedure

Following the synthetic procedure of 6a as described in Example 1, compound 6c (67% yield) was synthesized from benzo[d]isothiazol-3-one and allyl isocyanate as a white solid. mp 116-119° C.; IR(CHCl3) 3290, 1711, 1664, 1537 cm−1; 1H-NMR (CDCl3) δ 4.05-4.10 (m, 2H), 5.18-5.34 (m, 2H), 5.83-5.99 (m, 1H), 7.43 (t, J=7.2 Hz, 1H), 7.58 (d, J=7.2 Hz, 1H), 7.70 (t, J=7.2 Hz, 1H), 8.02 (d, J=7.2 Hz, 1H), 8.99 (br s, 1H); ESIMS m/e 235 (M++1).

Sources & evidence

ORD record: ord-c505305c4bab42c283f4a3f7cf13d252
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595403B2

Linked notes

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