4-Chlorobenzoyl chloride → HCID 57991636, compound

HRID 556035Notes

Reaction equation

HRID 556035 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][C:23]([Cl:22])=[CH:24][CH:25]=2)=[N:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991636HCID 57991636, compoundYield 69.4%

Procedure

A procedure similar to that in Example 4 was used, 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and p-chlorobenzoyl chloride were used as starting materials, the resulting crude product was recrystallized with acetone to obtain a product as a white solid in a yield of 69.4%, mp: 182-183 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.78 (3H, s, OCH3), 4.21 (2H, s, CH2), 6.75 (2H, d, J=7.56 Hz, ArH), 7.22˜7.35 (9H, m, ArH), 7.60 (2H, d, J=7.56 Hz, ArH), 11.70 (1H, br, CONH); EI-MS m/e (%): 434.2 (M+, 100), 123.0 (83); HREI-MS Calcd. for C24H19ClN2O2S: 434.0856. found: 434.0859. Anal. Calcd. for C24H19ClN2O2S: C, 66.28; H, 4.40; N, 6.44. found: C, 65.91; H, 4.22; N, 6.50.

Workup

  1. customthe resulting crude product was recrystallized with acetone

Sources & evidence

ORD record
ord-d72442bcbe0148dd88cc6afbd10e5743
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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