Hydrochloric Acid → HCID 13578786, compound

HRID 980225Notes

Reaction equation

HRID 980225 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:12](=[O:14])[CH3:13].[O:15]=[C:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([F:29])([F:28])[F:27])[C:20]=2[N:19]=[C:18]([CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[O:17]1.Cl>CCCCCC.O1CCCC1.O>[O:15]=[C:16]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([F:29])([F:28])[F:27])[C:20]=1[NH:19][C:18](=[O:17])[CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:37])[CH3:36])[CH2:13][C:12](=[O:14])[NH:11][C:7]1[S:6][CH:10]=[CH:9][N:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 176252-AcetamidothiazoleHCID 13578774HCID 13578774, compoundHCID 178418339Butyllithium

Product 1

HCID 13578786HCID 13578786, compoundYield 52.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-75 °C

Procedure

A solution of 85.6 ml of n-butyllithium in hexane was introduced into 8.5 g of N-2-thiazolyl acetamide suspended in 260 ml of tetrahydrofuran. After cooling to -75° C., a solution of 10.33 g of the product of Step A in 75 ml of tetrahydrofuran was added at this temperature. The reaction mixture was poured into 400 ml of water and 100 ml of 2N hydrochloric acid, and was extracted with ether. The organic phase was washed with N hydrochloric acid, then with water, dried, and concentrated to dryness under reduced pressure. The orange oil residue crystallized and the residue was triturated in ether, separated, washed with ether, and dried under reduced pressure to obtain 7.7 g of 1,1-dimethylethyl N-[2-[[2-[1,3-dioxo-3-(2-thiazolylamino)-propyl]-6-trifluoromethylphenyl]-amino]-2-oxo-ethyl]-carbamate melting at 166° C.

Workup

  1. extractionwas extracted with ether
  2. washThe organic phase was washed with N hydrochloric acid
  3. dry with materialwith water, dried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe orange oil residue crystallized
  6. customthe residue was triturated in ether
  7. customseparated
  8. washwashed with ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-af07b7d8456045caabff3132a407e26c
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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