Veratroyl chloride → HCID 5072926, compound

HRID 556089Notes

Reaction equation

HRID 556089 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:15])[S:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:21](Cl)=[O:22]>>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:21]([NH:15][C:11]1[S:12][C:13]([CH3:14])=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1)=[O:22]

Participants

3

Reactant 2

HCID 77070Veratroyl chlorideHCID 6132284-(4-Methoxyphenyl)-5-methyl-1,3-thiazol-2(3H)-iminato

Product 1

HCID 5072926HCID 5072926, compoundYield 63.5%

Procedure

A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-methyl-thiazol-2-ylamine prepared in Example 52 and 3,4-dimethoxy-benzoyl chloride prepared in the step 1 of Example 12 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to give a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (20:1) to obtain a product as a white solid in a yield of 63.5%, mp: 174-175 └. 1H-NMR (CDCl3, 400 MHz) δ: 2.51 (3H, s, ArCH3), 3.83 (3H, s, OCH3), 3.92 (3H, s, OCH3), 3.95 (3H, s, OCH3), 6.82˜6.92 (3H, m, ArH), 7.42˜7.56 (4H, m, ArH), 10.83 (1H, br, CONH); EI-MS m/e (%): 384.0 (M+, 66), 165.0 (100); HREI-MS Calcd. for C20H20N2O4S: 384.1144. found: 384.1143. Anal. Calcd. for C20H20N2O4S: C, 62.48; H, 5.24; N, 7.29. found: C, 62.30; H, 5.19; N, 7.30.

Workup

  1. customto react at room temperature overnight
  2. customto give 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)

Sources & evidence

ORD record
ord-54fead8968d244b5b869be6883f8d93b
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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