Triethylamine → HCID 86600443, compound

HRID 2055737Notes

Reaction equation

HRID 2055737 reaction equation
C1(OP(N=[N+]=[N-])(=O)[O:9][C:10]2C=CC=CC=2)C=CC=CC=1.C([N:22](CC)CC)C.[S:27]1[CH:31]=[CH:30][C:29]([C:32]2(C(O)=O)[CH2:41][CH2:40][C:35]3([O:39][CH2:38][CH2:37][O:36]3)[CH2:34][CH2:33]2)=[CH:28]1>C1(OC)C=CC=CC=1>[N:22]([C:32]1([C:29]2[CH:30]=[CH:31][S:27][CH:28]=2)[CH2:33][CH2:34][C:35]2([O:36][CH2:37][CH2:38][O:39]2)[CH2:40][CH2:41]1)=[C:10]=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 69181461HCID 69181461, compound

Product 1

HCID 86600443HCID 86600443, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
95 °C

Procedure

Azidophosphoric acid diphenyl ester (15.4 g; 56 mmole) and triethylamine (5.66 g; 55 mmole) were added to 8-thiophen-3-yl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid (15 g; 56 mmole) dissolved in anisole (160 ml). The reaction mixture was heated for 2 hours to 90 to 100° C. On completion of the reaction (reaction monitored by thin layer chromatography), the mixture was purified by column chromatography (silica gel, 10% ethyl acetate in n-hexane). 6 g of 8-isocyanato-8-thiophen-3-yl-1,4-dioxa-spiro[4.5]decane were obtained (41%; colorless liquid).

Workup

  1. customOn completion of the reaction (reaction monitored by thin layer chromatography)
  2. customthe mixture was purified by column chromatography (silica gel, 10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-a13d7d588a5b4875bec4e810f5d7d856
Source dataset
uspto-grants-2008_02
Patent number
US07332519B2

Reaction notes

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