Thionyl Chloride → HCID 19836646, compound

HRID 476886Notes

Reaction equation

HRID 476886 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>ClCCl.CN(C=O)C.CC(C)=O.O>[Si:1]([O:18][CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:33]=[N+:34]=[N-:35])=[O:25])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 19836684HCID 19836684, compound

Product 1

HCID 19836646HCID 19836646, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Step A ##STR116## A solution of 4-(tert-butyldiphenylsilyloxy)methylbenzoic acid (2 g) in dry dichloromethane (25 ml) was treated with thionyl chloride (1.1 ml) and dry DMF (3 drops). After stirring for 2 hours at room temperature, any volatile material was removed in vacuo. The crude acid chloride thus obtained was taken up in acetone (25 ml) and mixed under stirring at 0° C. with a solution of sodium azide (0.97 g) in water (4 ml). After few minutes most of the acetone was removed in vacuo and the reaction mixture extracted with benzene. The organic extracts were washed with brine, dried and evaporated to small volume, leaving a concentrated solution of 4-(tert-butyldiphenylsilyloxy)methylbenzoyl azide, which was used as such for the following step; IR (film) 2155, 1705 cm-1.

Workup

  1. customany volatile material was removed in vacuo
  2. customThe crude acid chloride thus obtained
  3. additionmixed
  4. customAfter few minutes most of the acetone was removed in vacuo
  5. extractionthe reaction mixture extracted with benzene
  6. washThe organic extracts were washed with brine
  7. customdried
  8. customevaporated to small volume

Sources & evidence

ORD record
ord-3eda71329226413786265fd46f96f6b2
Source dataset
uspto-grants-1989_12
Patent number
US04886793

Reaction notes

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