Phenol → HCID 178465409, compound

HRID 1448616Notes

Reaction equation

HRID 1448616 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([N:14]1[C:18]([S:19]C(C2C=CC=CC=2)C2C=CC=CC=2)=[N:17][N:16]=[N:15]1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(O)C=CC=CC=1>>[CH2:1]([O:8][C:9]([NH:11][CH:12]([N:14]1[C:18]([SH:19])=[N:17][N:16]=[N:15]1)[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 20380211HCID 20380211, compound

Product 1

HCID 178465409HCID 178465409, compoundYield 62%

Procedure

TEA (63 ml.) was added to 9.4 g. (0.0211 M.) of 1-benzyloxycarbonylaminoethyl-5-diphenylmethylthiotetrazole and 9.4 g. (0.1 M.) phenol and left standing at room temperature for 31/2 hours. The TFA was then evaporated off at 40° C. (15 mm.). The resulting oily residue was added to 63 ml. of a 5% NaHCO3 solution and 30 ml. of ether and titrated with concentrated NaOH to pH 8.2. The phases were separated and the aqueous water phase was titrated to pH 2 with concentrated hydrochloric acid, extracted twice with 60 ml. ether and the ether was evaporated to give an oil. The oil was azeotroped with ethyl acetate and crystallized by scratching with a glass rod to give 1-benzyloxycarbonylaminoethyl-5-mercaptotetrazole which was washed with 100 ml. "Skellysolve-B". 3.67 g. (62% yield) was collected by filtration.

Workup

  1. customstanding at room temperature for 31
  2. custom2 hours
  3. customThe TFA was then evaporated off at 40° C. (15 mm.)
  4. additionThe resulting oily residue was added to 63 ml
  5. customThe phases were separated
  6. extractionextracted twice with 60 ml
  7. customether and the ether was evaporated
  8. customto give an oil
  9. customThe oil was azeotroped with ethyl acetate
  10. customcrystallized

Sources & evidence

ORD record
ord-ba5ebec5ee554d5db6d07033c5974b75
Source dataset
uspto-grants-1979_12
Patent number
US04180658

Reaction notes

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