1-Bromopropane → HCID 21264512, compound

HRID 567073Notes

Reaction equation

HRID 567073 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[NH:21][S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:29](Br)[CH2:30][CH3:31]>CC(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[N:21]([CH2:29][CH2:30][CH3:31])[S:22]([CH2:25][CH3:26])(=[O:23])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 21264526HCID 21264526, compound

Product 1

HCID 21264512HCID 21264512, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Analogously to Example 11b, 7.5 g (20 mmol) of 6-benzyloxy-4-(ethylsulfonyl)amino-2,2-dimethylchroman (Example 11a) were introduced in portions at 10° C. into a suspension of 0.82 g (27 mmol) of sodium hydride (80% dispersion) in 100 ml of DMA. After stirring at RT for 2 h, 2.4 ml (26.2 mmol) of 1-propyl bromide were added dropwise. After work-up, the residue was chromatographed on silica gel using n-heptane/EA (1:1) and 6.0 g of product were crystallized from appropriate fractions using petroleum ether, m.p. 102-103° C.

Workup

  1. customAfter work-up, the residue was chromatographed on silica gel
  2. customwere crystallized from appropriate fractions

Sources & evidence

ORD record
ord-333c07fffe384a30b2ff3c6de494fe17
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

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