Water → HCID 21186245, compound

HRID 361462Notes

Reaction equation

HRID 361462 reaction equation
CS(Cl)(=O)=O.O[CH2:7][C:8]([NH:11][C:12](=[O:23])[CH:13]([CH3:22])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)([CH3:10])[CH3:9].C(N(CC)CC)C.O>ClCCl>[Br:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:13]([C:12]2[O:23][CH2:7][C:8]([CH3:9])([CH3:10])[N:11]=2)[CH3:22])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21186313HCID 21186313, compound

Product 1

HCID 21186245HCID 21186245, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphonyl chloride (11.4 g) in dichloromethane (50 ml) was added dropwise over 1 hour to a stirred mixture of N-(1-hydroxy-2-methylpropan-2-yl)-3-(4-bromophenyl)-2-methylpropionamide (31.4 g) and triethylamine (20.2 g) in dichloromethane (400 ml). The mixture was stirred for 2.5 hours and then water (300 ml) was added. The organic phase was separated, washed with water (200 ml) and saturated sodium chloride solution (200 ml) and dried (MgSO4). Volatile material was removed by evaporation to give 2-[1-(4-bromophenyl)propan-2-yl]-4,4-dimethyloxazoline(26.4 g) as a syrup; 1H NMR (CDCl3): 1.15 (d, 3 H), 1.2 (s, 3 H), 1.25 (s, 3 H), 2.25-2.35 (m, 2 H), 2.95-3.0 (m, 1 H), 3.85 (s, 2 H), 7.05 (d, 2 H), 7.4 (d, 2 H).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (200 ml) and saturated sodium chloride solution (200 ml)
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-5ef97e7c8db04710935e5ca1b10f9c61
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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