4-Cyanobenzoyl chloride → 4-cyano-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamide

HRID 556047Notes

Reaction equation

HRID 556047 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:24])[S:12][C:13]=2[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[C:25]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)#[N:26]>>[C:25]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:24][C:11]2[S:12][C:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=2)=[O:32])=[CH:29][CH:28]=1)#[N:26]

Participants

3

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 579916084-(4-Methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

Product 1

HCID 579915804-cyano-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamideYield 26.8%

Procedure

A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine prepared in Example 6 and p-cyanobenzoyl chloride prepared in the step 1 of Example 13 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (20:1-10:1) to obtain a product as a yellow solid in a yield of 26.8%, mp: 190-192└. 1H-NMR (CDCl3, 400 MHz) δ: 3.80 (3H, s, OCH3), 4.32 (2H, s, CH2), 6.75 (2H, d, J=8.72 Hz, ArH), 7.25 (2H, d, J=8.68 Hz, ArH), 7.37 (2H, d, J=8.68 Hz, ArH), 7.59 (2H, d, J=8.40 Hz, ArH), 7.82 (2H, d, J=8.40 Hz, ArH), 8.19 (2H, d, J=8.72 Hz, ArH); EI-MS m/e (%): 470.1 (M+, 100), 130.0 (76); HREI-MS Calcd. for C25H18N4O4S: 470.1049. found: 470.1050. Anal. Calcd. for C25H18N4O4S: C, 63.82; H, 3.86; N, 11.91. found: C, 64.16; H, 3.68; N, 12.19.

Workup

  1. customto react at room temperature overnight
  2. customto obtain a crude product, which
  3. customwas purified by a silica gel column chromatography
  4. washeluted with a gradient of dichloromethane and ethyl acetate (20:1-10:1)

Sources & evidence

ORD record
ord-d727922618f14635ac46e791e1e19117
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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