Hydrogen Peroxide → HCID 149148934, compound

HRID 1730668Notes

Reaction equation

HRID 1730668 reaction equation
[OH:1]O.[C:3]([NH:8][C:9]1[CH:14]=[C:13]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[NH:22][C:23]([NH:29][C:30]([O:32][CH3:33])=[O:31])=[N:24]C(OC)=O)(=[O:7])[CH2:4][CH2:5][CH3:6].[C:34]([O:37][C:38](=O)C)(=[O:36])C>>[C:3]([NH:8][C:9]1[CH:14]=[C:13]([S:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:1])[CH:12]=[CH:11][C:10]=1[N:22]([C:34]([O:37][CH3:38])=[O:36])[C:23]([NH:29][C:30]([O:32][CH3:33])=[O:31])=[NH:24])(=[O:7])[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 178454472HCID 178454472, compound

Product 1

HCID 149148934HCID 149148934, compound

Procedure

2.3 ml of H2O2 (30%) are added dropwise to a solution of 8.9 g of N-(2-butyramido-4-phenylthiophenyl)-N',N"-bis-methoxycarbonyl-guanidine (m.p. 155° C, Example 4) in 1.4 1 of acetic acid anhydride. After 10 hours the batch is concentrated in vacuo, a mixture of ethyl acetate and petroleum ether added to the residue and filtered. 8.5 g of N-(2-butyramido-4-phenylsulphinylphenyl)-N,N'-bis-methoxycarbonyl-guanidine are obtained with a m.p. of 186° C (decomp.), (redissolved from methanol/ethyl acetate). The mass spectrum shows a mol peak of 460.

Workup

  1. concentrationAfter 10 hours the batch is concentrated in vacuo
  2. additiona mixture of ethyl acetate and petroleum ether
  3. additionadded to the residue
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c3661347af8642de88a442efb36f4cf2
Source dataset
uspto-grants-1976_11
Patent number
US03993682

Reaction notes

Loading…