Veratroyl chloride → HCID 57991585, compound

HRID 556060Notes

Reaction equation

HRID 556060 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][C:9]2[S:13][C:12]([NH2:14])=[N:11][C:10]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28](Cl)=[O:29]>>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28]([NH:14][C:12]1[S:13][C:9]([CH2:8][C:7]2[CH:21]=[CH:22][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]=1)=[O:29]

Participants

3

Reactant 2

HCID 77070Veratroyl chlorideHCID 57991611HCID 57991611, compound

Product 1

HCID 57991585HCID 57991585, compoundYield 64.7%

Procedure

A procedure similar to that in Example 4 was used. 5-(4-nitro-benzyl)-4-phenyl-thiazol-2-ylamine prepared in Example 26 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 obtain a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (100:0-10:1) to obtain a product as a white solid in a yield of 64.7%, mp: 105-106 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.90 (3H, s, OCH3), 3.96 (3H, s, OCH3), 4.35 (2H, s, CH2), 6.85 (1H, t, J=8.68 Hz, ArH), 7.30˜7.48 (9H, m, ArH), 8.18 (2H, t, J=8.68 Hz, ArH), 10.21 (1H, br, CONH); EI-MS m/e (%): 475.0 (M+, 20), 165.0 (100); HREI-MS Calcd. for C25H21N3O5S: 475.1202. found: 475.1210.

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 (100:0-10:1)

Sources & evidence

ORD record
ord-0aa8323549524823a7631aae2980a029
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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