Ticlatone → HCID 11266104, compound

HRID 736632Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[NH:7][S:8][C:4]=2[CH:3]=1.[CH2:12]([N:16]=[C:17]=[O:18])[CH2:13][CH2:14][CH3:15]>>[CH2:12]([NH:16][C:17]([N:7]1[C:6](=[O:9])[C:5]2[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=2[S:8]1)=[O:18])[CH2:13][CH2:14][CH3:15]

Participants

Reactant 2

HCID 6258Ticlatone

HCID 8110Butyl isocyanate

Product 1

HCID 11266104HCID 11266104, compound

Procedure

Following the synthetic procedure of 6a as described in Example 1, compound 6w (90% yield) was synthesized from 6-chloro-benzo[d]isothiazol-3-one and n-butyl isocyanate as a white solid. IR(CHCl3) 3294, 1713, 1540 cm−1; 1H-NMR (DMSO-d6) δ0.89 (t, J=7.3 Hz, 3H), 1.26-1.37 (m, 2H), 1.47-1.55 (m, 2H), 3.28-3.34 (m, 2H), 7.50 (d, J=8.3 Hz, 1H), 7.91 (d, J=8.3 Hz, 1H), 8.14 (s, 1H), 8.76 (t, J=5.6 Hz, 1H); ESIMS m/e 284 and 286 (M++1, 35Cl and 37Cl).

Sources & evidence

ORD record: ord-74c3c2c81b064d77869cadd39e71f29b
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595403B2

Reaction notes

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