Dimethylformamide → HCID 131726770, compound

HRID 2055071Notes

Reaction equation

HRID 2055071 reaction equation
[C:1]([C:5]1[CH:23]=[C:22]([O:24][SiH:25]([CH3:27])[CH3:26])[C:8]2[N:9]=[C:10]([C:12]3[S:13][C:14]([CH3:21])([CH3:20])[CH:15]([C:17](O)=[O:18])[N:16]=3)[S:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:31])=O.CN(C)C=O>C(Cl)Cl>[C:1]([C:5]1[CH:23]=[C:22]([O:24][SiH:25]([CH3:27])[CH3:26])[C:8]2[N:9]=[C:10]([C:12]3[S:13][C:14]([CH3:21])([CH3:20])[CH:15]([C:17]([Cl:31])=[O:18])[N:16]=3)[S:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 131726771HCID 131726771, compound

Product 1

HCID 131726770HCID 131726770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

2-(6-tert.-butyldimethylsilyloxybenzothiazole-2-yl)-4,5-dihydro-5,5-dimethyl-4-thiazole carboxylic acid is dissolved under argon atmosphere in 8 ml dry methylene chloride, the clear solution is cooled to −15° C. and a mixture of 0.162 ml (1,875 mmol) oxalyl chloride and 500 μl of freshly distilled dimethyl formamide are added dropwise to the reaction under vigorous stirring. Slight gas emission can be observed during this step. The reaction mixture is stirred for additional 30 minutes at −15° C. and subsequently diluted with freshly destilled methylene chloride to a final volume of 30 ml.

Workup

  1. additionare added dropwise to the reaction under vigorous stirring

Sources & evidence

ORD record
ord-395d84768c4c4a64838ce108553976b5
Source dataset
uspto-grants-2008_02
Patent number
US07332354B2

Reaction notes

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