Oxalic Acid → HCID 54323423, compound

HRID 1886313Notes

Reaction equation

HRID 1886313 reaction equation
C(#N)C.O([C:11]([NH:13][C:14]1[CH:15]=[C:16]([C:20]2[N:21]([CH3:26])[N:22]=[N:23][C:24]=2[SH:25])[CH:17]=[CH:18][CH:19]=1)=[O:12])C1C=CC=CC=1.C(O)(=O)C(O)=O.[NH2:33][CH2:34][CH2:35][CH2:36][P:37](=[O:44])([O:41][CH2:42][CH3:43])[O:38][CH2:39][CH3:40]>C(N(CC)CC)C>[CH2:42]([O:41][P:37]([CH2:36][CH2:35][CH2:34][NH:33][C:11](=[O:12])[NH:13][C:14]1[CH:15]=[C:16]([C:20]2[N:21]([CH3:26])[N:22]=[N:23][C:24]=2[SH:25])[CH:17]=[CH:18][CH:19]=1)([O:38][CH2:39][CH3:40])=[O:44])[CH3:43]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 6342AcetonitrileHCID 78113Diethyl (3-aminopropyl)phosphonateHCID 19875684HCID 19875684, compound

Product 1

HCID 54323423HCID 54323423, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

40 ml of acetonitrile was added to 5.0 g of 4-(3-phenoxycarbonylaminophenyl)-3-methyl-5-mercaptotriazole (6) prepared in Step 1-5. 8.2 g of triethylamine was added to the system. 4.1 g of oxalic acid salt of diethyl 3-aminopropylphosphonate (8) prepared in Step 1-7 was added to the system. The system was then allowed to undergo reaction at a temperature of 50° C. over 4 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure. 100 ml of water was added to the residue to deposit 62 g of a crystal of 4-[3-{3-(3-diethylphosphonopropyl)ureido}phenyl]-3-methyl-5-mercaptotriazole (9). (Yield: 94%; m.p. 128° C.)

Workup

  1. customreaction at a temperature of 50° C. over 4 hours
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. addition100 ml of water was added to the residue

Sources & evidence

ORD record
ord-052f9cd2f2794d7798b4b9471d335c04
Source dataset
uspto-grants-1992_09
Patent number
US05151357

Reaction notes

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