4-(Propan-2-yl)benzene-1-sulfonyl chloride → HCID 16045797, compound

HRID 1410186Notes

Reaction equation

HRID 1410186 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH2:22])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH:23]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)([CH3:25])[CH3:24]>N1C=CC=CC=1.C(Cl)Cl.C(OC(=O)C)C>[NH2:22][C:10]1[N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH:12]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][S:32]([C:29]3[CH:30]=[CH:31][C:26]([CH:23]([CH3:25])[CH3:24])=[CH:27][CH:28]=3)(=[O:34])=[O:33])[CH:7]=[CH:6][CH:5]=2)[N:9]=1

Participants

6

Reactant 2

HCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 16045798HCID 16045798, compound

Product 1

HCID 16045797HCID 16045797, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

55.1 A solution of 100 mg 4-(3-aminophenyl)-1-(2-methoxybenzyl)-1H-imidazole-2-ylamine (0.34 mmol, Example 51) in 3 mL pyridine was combined with 74 mg 4-isopropylbenzenesulfonic acid chloride at 0° C., then stirred for 18 hr at room temperature. The batch was then diluted with methylene chloride, extracted with 1 M NaOH and with water, and the organic phase was then dried (Na2SO4) and concentrated, and the residue thus obtained was stirred in acetic ethyl ester, suctioned off, and dried (130 mg target product).

Workup

  1. extractionextracted with 1 M NaOH and with water
  2. dry with materialthe organic phase was then dried (Na2SO4)
  3. concentrationconcentrated
  4. customthe residue thus obtained
  5. customdried (130 mg target product)

Sources & evidence

ORD record
ord-329bc2956ae04878afd0662132357274
Source dataset
uspto-grants-2014_12
Patent number
US08921406B2

Reaction notes

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