Oxalyl chloride → HCID 22324121, compound

HRID 495967Notes

Reaction equation

[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][CH:9]1[C:15]([OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:21])=O>>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][CH:9]1[C:15]([Cl:21])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 65578Oxalyl chloride

HCID 13543370HCID 13543370, compound

Product 1

HCID 22324121HCID 22324121, compoundYield 92.2%

Procedure

To (RS)-4-benzyl-5-oxo-morpholine-3-carboxylic acid (2.0 g, 8.51 mmol) in MDC (40 ml) was slowly added oxalyl chloride (1.51 ml, 17.1 mmol). The mixture was stirred for 0.5 h at room temperature and then evaporated to give (RS)-4-benzyl-5-oxomorpholine-3-carbonyl chloride as a brown solid (1.99 g, 92%). Ammonia gas was bubbled steadily through a solution of (RS)-4-benzyl-5-oxomorpholine-3-carbonyl chloride (1.99 g, 7.79 mmol) in MDC (40 ml) at 0° C. for 0.5 h, and then the mixture allowed to warm to room temperature. The solid was collected by filtration, washed with MDC (30 ml) and dried in vacuo at 40° C. to give the title compound as a white solid (2.1 g, 99%). Mass spectrum (API+): Found 235 (MH30 ). C12H14N2O3 requires 234.

Workup

customevaporated

Sources & evidence

ORD record: ord-32c774d19500477fa4c6817f962c60d8
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06943160B2

Reaction notes

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