Cyclohexane, (bromomethyl)- → HCID 14865018, compound

HRID 1194891Notes

Reaction equation

HRID 1194891 reaction equation
Cl.[OH:2]/[N:3]=[C:4](/[C:10]1[N:11]=[C:12]([NH:15]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:13][CH:14]=1)\[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:35]1([CH2:41]Br)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(O)=O>[NH2:15][C:12]1[S:13][CH:14]=[C:10](/[C:4](=[N:3]/[O:2][CH2:41][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:11]=1

Participants

4

Reactant 2

HCID 137636Cyclohexane, (bromomethyl)-HCID 9589415(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate hydrochloride

Product 1

HCID 14865018HCID 14865018, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Ethyl (Z)-2-(hydroxyimino)-2-(2-tritylaminothiazol-4-yl)acetate hydrochloride (3.08 g) was reacted with cyclohexylmethyl bromide as described in Example 5a. The product was deprotected with formic acid as described in Example 1a. Crystallisation from cyclohexane/hexane gave the title compound as a white solid (1.2 g, 62%), m.p. 107.0°-107.5° C. [Found: C: 54.21; H: 6.58; N: 13.31. C14H21N3O3S requires C: 54.00; H: 6.80; N: 13.49%]. νmax (CHCl3) 3400, 2920, 1730, 1600 cm-1 ; δH (CDCl3) 1.0 (2H, m), 1.2 (3H, m), 1.33 (3H, t), 1.7 (6H, m), 3.97 (2H, d), 4.35 (2H, q), 5.60 (2H, br s, exch. D2O), 6.63 (1H, s).

Workup

  1. customCrystallisation from cyclohexane/hexane

Sources & evidence

ORD record
ord-44cb25cbf7c14860a45e1235ba8da6dd
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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