Tributyltin azide → 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-(2-tribut-1-ylstannyltetrazol-5-yl)propan-2-ol

HRID 1979917Notes

Reaction equation

HRID 1979917 reaction equation
[CH2:1]([Sn:5]([N:14]=[N+:15]=[N-:16])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[C:17]([CH2:19][C:20]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[Cl:35])([OH:27])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)#[N:18]>>[Cl:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[C:20]([OH:27])([CH2:19][C:17]1[N:16]=[N:15][N:14]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:1][CH2:2][CH2:3][CH3:4])[N:18]=1)[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1

Participants

3

Reactant 2

HCID 4984872Tributyltin azide2×HCID 133903931-Cyano-2-(2,4-Dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-2-propanol

Product 1

HCID 133903942-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-(2-tribut-1-ylstannyltetrazol-5-yl)propan-2-olYield 73.2%

Procedure

A paste of tri-n-butyltin azide (2.45 g) and 1-cyano-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (2.0 g) was heated at 160° C. for three hours. A further quantity of tri-n-butyltin azide (0.2 g) was added and the heating continued for a further hour to complete the reaction. The resulting viscous oil was triturated with ethyl acetate and the product collected and dried under vacuum to give 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-(2-tribut-1-ylstannyltetrazol-5-yl)propan-2-ol as a crystalline solid (3.1 g, 73%) m/e 628.

Workup

  1. waitthe heating continued for a further hour
  2. customthe reaction
  3. customThe resulting viscous oil was triturated with ethyl acetate
  4. customthe product collected
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f73ab9722da74f94b208f291f25e057a
Source dataset
uspto-grants-1984_11
Patent number
US04483863

Reaction notes

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