Water → 5-Isothiocyanato-2-(1-methyl-1H-pyrrol-2-yl)-1,3-benzoxazole

HRID 1576868Notes

Reaction equation

HRID 1576868 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[N:11]([CH3:15])[CH:12]=[CH:13][CH:14]=3)=[N:7][C:6]=2[CH:16]=1.[C:17](Cl)(Cl)=[S:18].C(=O)([O-])[O-].[Ca+2].O>C(Cl)(Cl)Cl>[CH3:15][N:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([N:1]=[C:17]=[S:18])=[CH:16][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 215056582-(1-Methyl-1H-pyrrol-2-yl)-1,3-benzoxazol-5-amine

Product 1

HCID 127819245-Isothiocyanato-2-(1-methyl-1H-pyrrol-2-yl)-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1.0 g of 5-amino-2-(1-methyl-2-pyrrolyl)benzoxazole (0.0047 mole) is dissolved in 50 ml of chloroform and slowly added to the following cold mixture: 0.54 g of thiophosgene (0.0047 mole), 0.47 g of calcium carbonate (0.0047 mole), 100 ml of chloroform and 25 ml of water. After the addition is complete the reaction is stirred at room temperature for 2 hr. The chloroform layer is separated, dried over anhyd. MgSO4 and evaporated under vacuum yielding a light brown solid. This material is crystallized from petroleum ether yielding 0.650 g of tan crystals, mp 105°-106° (54%).

Workup

  1. additionslowly added to the following cold mixture
  2. additionAfter the addition
  3. customThe chloroform layer is separated
  4. customdried over anhyd
  5. customMgSO4 and evaporated under vacuum
  6. customyielding a light brown solid
  7. customThis material is crystallized from petroleum ether yielding 0.650 g of tan crystals, mp 105°-106° (54%)

Sources & evidence

ORD record
ord-ef08b24cda134d4eadc0507081fb4258
Source dataset
uspto-grants-1976_09
Patent number
US03983130

Reaction notes

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