Water → HCID 178441189, compound

HRID 1074277Notes

Reaction equation

HRID 1074277 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][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][C:27]1[NH:31][N:30]=[N:29][N:28]=1.S(Cl)(Cl)=O.O>N1C=CC=CC=1>[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][C:13]([C:14]([NH:26][C:27]2[NH:31][N:30]=[N:29][N:28]=2)=[O:15])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 14850618HCID 14850618, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178441189HCID 178441189, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2.00 g (5.9 mmole) of 4-(3,5-di-t-butylphenoxymethyl)benzoic acid and 0.61 g (5.9 mmole) of 5-aminotetrazole in 20 ml of pyridine was treated with a dropwise addition of 1.40 g (11.8 mmole) of thionyl chloride. The solution was stirred for one and a half hours before being poured into 150 ml of water. The resulting precipitate was collected, rinsed with water, air dried and recrystallized from aqueous dimethylformamide to give 1.4 g of white solid 4-(3,5-di-t-butylphenoxymethyl)-N-(tetrazol-5-yl)benzamide, m.p. >290° C. Analysis: Calculated for: C23H29N5O2 ; %C, 67.6; %H, 7.1; %N, 17.2; Found: %C, 67.8; %H, 7.3; %N, 17.6.

Workup

  1. customThe resulting precipitate was collected
  2. washrinsed with water, air
  3. customdried
  4. customrecrystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-fe60e6d2673b40378d799c5712288b2e
Source dataset
uspto-grants-1990_11
Patent number
US04973731

Reaction notes

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