4-Chlorobenzyl mercaptan → HCID 71270229, compound

HRID 927063Notes

Reaction equation

HRID 927063 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:4]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:3]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][SH:36])=[CH:31][CH:30]=1.CCN(C(C)C)C(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][S:36][C:2]2[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)=[C:4]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH:3]=2)=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 804094-Chlorobenzyl mercaptanHCID 81531DiisopropylethylamineHCID 86677026HCID 86677026, compound2×

Product 1

HCID 71270229HCID 71270229, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 6-chloro-3,4-bis[(4-methoxybenzyl)oxy]pyridazine (Intermediate 7; 550 mg, 1.42 mmol), (4-chlorophenyl)methanethiol (248 mg, 1.56 mmol), Pd2(DBA)3 (52.1 mg, 0.057 mmol), XANTPHOS (65.8 mg, 0.114 mmol) and Hunig's base (ethyl diisopropylamine; 404 mg, 3.13 mmol) was subjected to microwave irradiation at 120° C. for 1 hour. The resulting mixture was poured into water and extracted into ethyl acetate before the combined organics were washed with brine and then dried (magnesium sulphate). The resulting solution was evaporated in vacuo and purified by silica chromatography (eluting with 0-40% dichlormethane in petrol) to yield 6-[(4-chlorobenzyl)sulfanyl]-3,4-bis[(4-methoxybenzyl)oxy]pyridazine (201 mg, 1.42 mmol, 28% yield).

Workup

  1. customirradiation at 120° C. for 1 hour
  2. extractionextracted into ethyl acetate before the combined
  3. washorganics were washed with brine
  4. dry with materialdried (magnesium sulphate)
  5. customThe resulting solution was evaporated in vacuo
  6. custompurified by silica chromatography (eluting with 0-40% dichlormethane in petrol)

Sources & evidence

ORD record
ord-7adcdf7235f545c788a0c57adc2de7e9
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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