Thiocyanic acid → 4,5-Diphenyl-2-oxazolyl mercaptoacetic acid

HRID 1580804

Reaction equation

HRID 1580804 reaction equation
S[C:2]1[O:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C1(C2N[C:27](=[O:36])[O:28]C=2C2C=CC=CC=2)C=CC=CC=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.[SH:67][C:68]#N.[H-].[Na+].BrCC(O)=O>O.CN(C=O)C.C1(C)C(C)=CC=CC=1.CO>[C:7]1([C:5]2[N:6]=[C:2]([CH:68]([SH:67])[C:27]([OH:36])=[O:28])[O:3][C:4]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

12

Reactant 7

HCID 781Thiocyanic acidHCID 6227Bromoacetic AcidHCID 8400BenzoinHCID 14817Phosphorus sulfide (P2S5)HCID 24758Sodium hydrideHCID 1512454,5-Diphenyl-4-oxazolin-2-oneHCID 178527826HCID 178527826, compound

Product 1

HCID 214083604,5-Diphenyl-2-oxazolyl mercaptoacetic acid

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 7237O-XyleneSolvent

Procedure

12 g. of 2-mercapto-4,5-diphenyl-oxazole (m.p. 252°-254°, from methanol; obtainable from 4,5-diphenyl-2-oxazolone and phosphorus pentasulfide in boiling xylene, or by the reaction of benzoin with HSCN) is dissolved in 100 ml. of DMF, and 1.2 g. of NaH is added thereto. The reaction mixture is agitated for 1.5 hours at room temperature. Then, 5.6 ml. of the ethyl ester of bromoacetic acid in 20 ml. of DMF is added dropwise thereto, and the reaction mixture is stirred for 2 hours at 80°. The mixture is then mixed with water and worked up as usual, thus obtaining the ethyl ester of 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid, b.p. 207°-210°/0.1 mm.; m.p. 54°-56° (hexane).

Workup

  1. dissolutionis dissolved in 100 ml
  2. stirringthe reaction mixture is stirred for 2 hours at 80°

Sources & evidence

ORD record
ord-48d6f71e58f743a39566282b6eeb664d
Source dataset
uspto-grants-1976_01
Patent number
US03933840

Linked notes

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