Thionyl Chloride → HCID 178441188, compound

HRID 1074279Notes

Reaction equation

HRID 1074279 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)[O:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13])([CH3:4])([CH3:3])[CH3:2].[NH2:26][C:27]1[NH:31][N:30]=[N:29][N:28]=1.S(Cl)(Cl)=O>N1C=CC=CC=1.Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)[O:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([NH:26][C:27]1[NH:31][N:30]=[N:29][N:28]=1)=[O:13])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 15067988HCID 15067988, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178441188HCID 178441188, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

A solution of 3.40 g (0.01 mole) of 2-(3,5-di-t-butylphenoxymethyl)benzoic acid and 1.03 g (0.01 mole) of 5-aminotetrazole in 30 ml of pyridine was treated with a dropwise addition of 2.36 g (0.02 mole) of thionyl chloride. The resulting solution was stirred for forty minutes before being diluted with 300 ml of 5% hydrochloric acid to give a gum which slowly crystallized. The solid was collected, rinsed with water and recrystallized from aqueous dimethylformamide to give 1.3 g of white solid 2-(3,5-di-t-butylphenoxymethyl)-N-(tetrazol-5-yl)benzamide, m.p. 251°-254° C.. Analysis: Calculated for C23H29N5O2 : %C, 67.8; %H, 7.2; %N, 17.2; Found: %C, 67.7; %H, 7.1; %N, 17.2.

Workup

  1. customto give a gum which
  2. customslowly crystallized
  3. customThe solid was collected
  4. washrinsed with water
  5. customrecrystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-b161bb600b744367a17e8b56478f12b2
Source dataset
uspto-grants-1990_11
Patent number
US04973731

Reaction notes

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