Ethyl chloroformate → 2-Cyanoethyl-5-ethoxycarbonylamino-2,3-dihydrobenzofuran

HRID 582616Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH2:10][CH2:11][C:12]#[N:13])[CH2:7][C:6]=2[CH:14]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])O.[Na+]>>[C:12]([CH2:11][CH2:10][CH:8]1[CH2:7][C:6]2[CH:14]=[C:2]([NH:1][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=[CH:4][C:5]=2[O:9]1)#[N:13]

Participants

Reactant 3

HCID 10928Ethyl chloroformate

HCID 516892Sodium Bicarbonate

HCID 545014885-Amino-2-cyanoethyl-2,3-dihydrobenzofuran

Product 1

HCID 538067322-Cyanoethyl-5-ethoxycarbonylamino-2,3-dihydrobenzofuranYield 87.8%

Procedure

Starting from 2.6 g (14 mmol) of 5-amino-2-cyanoethyl-2,3-dihydrobenzofuran, 1.45 ml (15.2 mmol) of ethyl chloroformate and 1.7 g (21 mmol) of sodium hydrogencarbonate treated under the conditions described in step 6 of Example 1, 3.2 g of product were obtained.

Workup

additiontreated under the conditions

Sources & evidence

ORD record: ord-033a5d688db6423b8f1d6a17f63b2bdc
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05925662

Reaction notes

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