Carbon Disulfide → HCID 178497011, compound

HRID 2039628Notes

Reaction equation

HRID 2039628 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([S:11][CH2:12]C[Si](C)(C)C)=[C:6]([Cl:18])[C:5]=1[NH2:19].COC(=O)C1C=C(N)C([SH:31])=C(Cl)C=1N.C(=S)=S.[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]([C:4]1[C:5]([NH2:19])=[C:6]([Cl:18])[CH:7]2[S:11][C:12]([SH:31])=[N:10][CH:8]2[CH:9]=1)=[O:20]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 57855980HCID 57855980, compoundHCID 57855982HCID 57855982, compound

Product 1

HCID 178497011HCID 178497011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound is synthesized as reported in U.S. Pat. No. 4,454,148. 2,5-Diamino-3-chloro-4-(2-trimethylsilanyl-ethylsulfanyl)-benzoic acid methyl ester (step d in example H17) is used as starting material and after thiol deprotection (step f in example H17), the crude 2,5-diamino-3-chloro-4-mercapto-benzoic acid methyl ester is cyclized with CS2, NaOH in EtOH at 70° C. The crude is directly used in the next step without further purification; LC/MS: 275/277 (M+1)+.

Workup

  1. customThis compound is synthesized
  2. customThe crude is directly used in the next step without further purification

Sources & evidence

ORD record
ord-95172c9ce7c54b4c86771240c98cfc0c
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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