p-Chlorothiophenol → HCID 23316275, compound

HRID 1982495Notes

Reaction equation

HRID 1982495 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([N+]([O-])=O)=[CH:4][C:3]=1[C:21]1[O:22][CH2:23][CH2:24][CH2:25][N:26]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([SH:40])=[CH:36][CH:35]=1>CN1CCCC1=O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([S:40][C:37]2[CH:38]=[CH:39][C:34]([Cl:33])=[CH:35][CH:36]=2)=[CH:4][C:3]=1[C:21]1[O:22][CH2:23][CH2:24][CH2:25][N:26]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 23316286HCID 23316286, compound

Product 1

HCID 23316275HCID 23316275, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

14 g of 1-amino-2-(5,6-dihydro-4H-1,3-oxazin-2-yl)-4-nitroanthraquinone, 5.4 g of potassium carbonate, 100 cc of N-methylpyrrolidone and 5.9 g of 4-chlorothiophenol are reacted as in Example 2. The reaction mixture is worked up as described in that example to give 9.2 g of 1-amino-2-(5,6-dihydro-4H-1,3-oxazin-2-yl)-4-(4-chlorophenylmercapto)-anthraquinone, corresponding to a yield of 51% of theory.

Sources & evidence

ORD record
ord-e2ea3168ed3c4a1e89852773883201dd
Source dataset
uspto-grants-1986_06
Patent number
US04596666

Reaction notes

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