Hydrochloric Acid → HCID 178498869, compound

HRID 2051704Notes

Reaction equation

HRID 2051704 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH:4]([NH2:7])[CH:5]=O.COC(=O)C(C([CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O)N.[S-:30][C:31]#[N:32].[K+].Cl>O.O1CCCC1>[CH:16]([N:7]1[C:4]([C:3]([O:2][CH3:1])=[O:8])=[CH:5][N:32]=[C:31]1[SH:30])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516872Potassium thiocyanateHCID 17923333HCID 17923333, compoundHCID 56997143HCID 56997143, compound

Product 1

HCID 178498869HCID 178498869, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

31.3 g (0.1 mol) of 2-benzhydrylformyl)-amino-3-oxopropionic acid methyl ester (prepared by formylation of (benzhydrylformyl)-aminoacetic acid methyl ester according to J. Am. Chem. Soc. 71, (1949), page 644, and 18 g of potassium thiocyanate were introduced into a mixture of 200 cc of tetrahydrofurane, 200 cc of water and 16.5 cc of 36% aqueous hydrochloric acid while stirring. Stirring was continued for 31/2 hours at 40° C.; then the organic phase was separated and the solvent removed under reduced pressure. The residue was taken up in methylene chloride and freed from acid residues by shaking twice with water. After washing with methanol, 29.8 g (92% of the theory) of 1-benzhydryl-2-mercapto-5-methoxy-imidazole melting at 194° C. were obtained.

Workup

  1. stirringStirring
  2. custom2 hours
  3. customat 40° C.
  4. customthen the organic phase was separated
  5. customthe solvent removed under reduced pressure
  6. stirringby shaking twice with water
  7. washAfter washing with methanol, 29.8 g (92% of the theory) of 1-benzhydryl-2-mercapto-5-methoxy-imidazole melting at 194° C.
  8. customwere obtained

Sources & evidence

ORD record
ord-4df741b65f714f01be42a83dc57f3b86
Source dataset
uspto-grants-1980_01
Patent number
US04182624

Reaction notes

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