Dichloromethane → HCID 66838440, compound

HRID 2079742Notes

Reaction equation

HRID 2079742 reaction equation
C(N(CC)CC)C.ClCCl.[CH:11]1([C:14](Cl)=[O:15])[CH2:13][CH2:12]1.C(OCC)(=O)C.[NH2:23][C:24]1[S:28][N:27]=[C:26]([Br:29])[C:25]=1[C:30](=[O:32])[CH3:31]>>[C:30]([C:25]1[C:26]([Br:29])=[N:27][S:28][C:24]=1[NH:23][C:14]([CH:11]1[CH2:13][CH2:12]1)=[O:15])(=[O:32])[CH3:31]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 77637Cyclopropanecarbonyl chlorideHCID 122461921-(5-Amino-3-bromo-1,2-thiazol-4-yl)ethan-1-one2×

Product 1

HCID 66838440HCID 66838440, compoundYield 60%

Conditions

Temperature
16 °C

Procedure

Add triethylamine (234.5; mL, 1.68; mol) to a cooled suspension of 1-(5-amino-3-bromo-isothiazol-4-yl)-ethanone (310; g, 1.40; mol) in dichloromethane (2.79; L, 43.53 mol) at 0° C. under nitrogen and then add slowly a solution of cyclopropanecarbonyl chloride (137.5; mL, 1.47; mol) in dichloromethane (310; mL, 4.84; mol) at 0° C. over 1 hour. Warm to 16° C. over 2; hours and then cool to 10° C., add water (1; L) and separate the layers. Extract the aqueous layer once with dichloromethane (500; mL). Combine the organic layers, concentrate and purify by silica gel chromatography eluting with n-hexane:dichloromethane 30:70. Triturate the recovered solid with hexanes to give the title compound as a white solid (256.1; g, 60%). MS (m/z): 289, 291; (M+1).

Workup

  1. temperaturehours and then cool to 10° C.
  2. customseparate the layers
  3. extractionExtract the aqueous layer once with dichloromethane (500; mL)
  4. concentrationCombine the organic layers, concentrate
  5. custompurify by silica gel chromatography
  6. washeluting with n-hexane:dichloromethane 30:70
  7. customTriturate the recovered solid with hexanes

Sources & evidence

ORD record
ord-548adc55b3a44913b7f14b0aa91d1731
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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