Ticlatone → HCID 11404203, compound

HRID 736633Notes

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:18]=[C:19]=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[CH2:12]([NH:18][C:19]([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:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

Reactant 2

HCID 6258Ticlatone

HCID 75659Hexyl isocyanate

Product 1

HCID 11404203HCID 11404203, compound

Procedure

Following the synthetic procedure of 6a as described in Example I, compound 6x (91% yield) was synthesized from 6-chloro-benzo[d]isothiazol-3-one and n-hexyl isocyanate as a white solid. IR(CHCl3) 3298, 1713, 1539 cm−1; 1H-NMR (CDCl3) δ0.89 (t, J=6.8 Hz, 3H), 1.28-1.43 (m, 6H), 1.60-1.68 (m, 2H), 3.40-3.46 (m, 2H), 7.38 (d, J=8.8 Hz, 1H), 7.58 (s, 1H), 7.93 (d, J=8.8 Hz, 1H), 8.77 (s, 1H); ESIMS m/e 313 and 315 (M++1, 35Cl and 37Cl).

Sources & evidence

ORD record: ord-306ad8f2c07e4b928faef1af4fdfe19f
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595403B2

Reaction notes

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